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Current Organic Chemistry

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ISSN (Print): 1385-2728
ISSN (Online): 1875-5348

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Review Article

Synthesis of Polynuclear Aromatic Hydrocarbons by Palladium-catalyzed C-H Bond Functionalization

Author(s): Mitali Dewan, Sachinath Bera, Shubhankar Samanta, Debasish Kundu* and Rathin Jana*

Volume 28, Issue 18, 2024

Published on: 21 June, 2024

Page: [1387 - 1403] Pages: 17

DOI: 10.2174/0113852728283702240605113835

Price: $65

Abstract

Nowadays palladium-catalyzed C–H bond activation is a useful approach for the synthetic transformation of organic compounds due to step economy, the use of non-prefunctionalized substrates and reduced chemical wastes. Among the various synthetic strategies, palladium catalyzed intra and inter-molecular C–H bond activation has recently drawn a lot of interest to synthesize the decorated π-conjugated polycyclic aromatic hydrocarbon. In this review, we have focused on recent progress along with previous strategies to synthesize various polynuclear aromatic hydrocarbons (PAHs) by the use of Pd-catalyzed C–H bond activation. We have also discussed the mechanistic details of the reaction intra and inter-molecular C–H bond activation.

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Graphical Abstract

[1]
Harvey, R.G. Polycyclic Aromatic Hydrocarbons; Wiley-VCH: New York, 1997, p. 667.
[2]
Harvey, R.G. Polycyclic Aromatic Hydrocarbons: Chemistry and Carcinogenicity; Cambridge University Press: Cambridge, 1991.
[3]
de Koning, C.B.; Michael, J.P.; Rousseau, A.L. A novel method for the synthesis of phenanthrenes and benzo[a]carbazoles. Tetrahedron Lett., 1998, 39(47), 8725-8728.
[http://dx.doi.org/10.1016/S0040-4039(98)01919-4]
[4]
Pathak, R.; Vandayar, K.; van Otterlo, W.A.L.; Michael, J.P.; Fernandes, M.A.; de Koning, C.B. The synthesis of angularly fused polyaromatic compounds by using a light-assisted, base-mediated cyclization reaction. Org. Biomol. Chem., 2004, 2(23), 3504-3509.
[http://dx.doi.org/10.1039/b412932f] [PMID: 15565244]
[5]
Harvey, R.G. Activated metabolites of carcinogenic hydrocarbons. Acc. Chem. Res., 1981, 14(7), 218-226.
[http://dx.doi.org/10.1021/ar00067a004]
[6]
Harvey, R.G.; Geacintov, N.E. Intercalation and binding of carcinogenic hydrocarbon metabolites to nucleic acids. Acc. Chem. Res., 1988, 21(2), 66-73.
[http://dx.doi.org/10.1021/ar00146a004]
[7]
Ritleng, V.; Sirlin, C.; Pfeffer, M. Ru-, Rh-, and Pd-catalyzed C-C bond formation involving C-H activation and addition on unsaturated substrates: Reactions and mechanistic aspects. Chem. Rev., 2002, 102(5), 1731-1770.
[http://dx.doi.org/10.1021/cr0104330] [PMID: 11996548]
[8]
Li, C.J. Quasi-nature catalysis: Developing C-C bond formations catalyzed by late transition metals in air and water. Acc. Chem. Res., 2002, 35(7), 533-538.
[http://dx.doi.org/10.1021/ar0100125] [PMID: 12118992]
[9]
Catellani, M.; Chiusoli, G.P. The terminations step in palladium-catalyzed insertion reactions. J. Organomet. Chem., 1983, 250(1), 509-515.
[http://dx.doi.org/10.1016/0022-328X(83)85074-8]
[10]
Oyamada, J.; Lu, W.; Jia, C.; Kitamura, T.; Fujiwara, Y. Direct synthesis of β-alkenylpyrroles by Pd(II)-catalyzed addition of pyrroles to alkynoates. Chem. Lett., 2002, 31(1), 20-21.
[http://dx.doi.org/10.1246/cl.2002.20]
[11]
Oyamada, J.; Jia, C.; Fujiwara, Y.; Kitamura, T. Direct synthesis of coumarins by Pd(II)-catalyzed reaction of alkoxyphenols and alkynoates. Chem. Lett., 2002, 31(3), 380-381.
[http://dx.doi.org/10.1246/cl.2002.380]
[12]
Jia, C.; Piao, D.; Kitamura, T.; Fujiwara, Y. New method for preparation of coumarins and quinolinones via Pd-catalyzed intramolecular hydroarylation of C-C triple bonds. J. Org. Chem., 2000, 65(22), 7516-7522.
[http://dx.doi.org/10.1021/jo000861q] [PMID: 11076610]
[13]
Fujiwara, Y.; Jia, C. Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley & Sons: New York, 2002, 1, p. 2859.
[http://dx.doi.org/10.1002/0471212466.ch133]
[14]
Jia, C.; Kitamura, T.; Fujiwara, Y. Catalytic functionalization of arenes and alkanes via C-H bond activation. Acc. Chem. Res., 2001, 34(8), 633-639.
[http://dx.doi.org/10.1021/ar000209h] [PMID: 11513570]
[15]
Karig, G.; Moon, M.T.; Thasana, N.; Gallagher, T. C-H activation and palladium migration within Biaryls under Heck reaction conditions. Org. Lett., 2002, 4(18), 3115-3118.
[http://dx.doi.org/10.1021/ol026426v] [PMID: 12201730]
[16]
Cámpora, J.; López, J.A.; Palma, P.; Valerga, P.; Spillner, E.; Carmona, E. Cleavage of palladium metallacycles by acids: A probe for the study of the cyclometalation reaction. Angew. Chem. Int. Ed., 1999, 38(1-2), 147-151.
[http://dx.doi.org/10.1002/(SICI)1521-3773(19990115)38:1/2<147::AID-ANIE147>3.0.CO;2-I]
[17]
Markies, B.A.; Wijkens, P.; Kooijman, H.; Spek, A.L.; Boersma, J.; van Koten, G. Insertion of norbornene into aryl–palladium(II) bonds: Mechanistic aspects of the subsequent C–H activation. J. Chem. Soc. Chem. Commun., 1992, (19), 1420-1423.
[http://dx.doi.org/10.1039/C39920001420]
[18]
Bocelli, G.; Catellani, M.; Chiusoli, G.P. Palladium-catalyzed C C bond formation involving aromatic CH activation: III. Aspects of aromatic substitution and structure of 1-bromo-3-[3-(2-methylenecyclohex-5-en-1-yl)bicyclo[2.2.1]hept-2-yl]-4-bicyclo[2.2.1]hept-2-ylbenzene. J. Organomet. Chem., 1985, 279, 225-232.
[http://dx.doi.org/10.1016/0022-328X(85)87020-0]
[19]
Song, L.; der Eycken, V.E.V. Transition metal‐catalyzed intermolecular cascade C−H activation/annulation processes for the synthesis of polycycles. Chemistry, 2021, 27(1), 121-144.
[http://dx.doi.org/10.1002/chem.202002110] [PMID: 32530508]
[20]
Guo, L.N.; Duan, X.H.; Liu, X.Y.; Hu, J.; Bi, H.P.; Liang, Y.M. Synthesis of fused polycycles from propargylic compounds with terminal alkynes via a palladium-catalyzed tandem C-H activation/biscyclization process. Org. Lett., 2007, 9(26), 5425-5428.
[http://dx.doi.org/10.1021/ol702311z] [PMID: 18031051]
[21]
Ren, Z.H.; Guan, Z.H.; Liang, Y.M. Highly regioselective synthesis of benz[a]anthracene derivatives via a Pd-catalyzed tandem C-H activation/biscyclization reaction. J. Org. Chem., 2009, 74(8), 3145-3147.
[http://dx.doi.org/10.1021/jo802712n] [PMID: 19284714]
[22]
Lu, Z.; Hu, C.; Guo, J.; Li, J.; Cui, Y.; Jia, Y. Water-controlled regioselectivity of Pd-catalyzed domino reaction involving a C-H activation process: Rapid synthesis of diverse carbo- and heterocyclic skeletons. Org. Lett., 2010, 12(3), 480-483.
[http://dx.doi.org/10.1021/ol902672a] [PMID: 20030345]
[23]
Campeau, L.C.; Fagnou, K. Palladium-catalyzed direct arylation of simple arenes in synthesis of biaryl molecules. Chem. Commun., 2006, (12), 1253-1264.
[http://dx.doi.org/10.1039/b515481m] [PMID: 16538241]
[24]
Pascual, S.; de Mendoza, P.; Echavarren, A.M. Palladium catalyzed arylation for the synthesis of polyarenes. Org. Biomol. Chem., 2007, 5(17), 2727-2734.
[http://dx.doi.org/10.1039/b707940k] [PMID: 17700837]
[25]
Song, J.; Li, Y.; Sun, W.; Yi, C.; Wu, H.; Wang, H.; Ding, K.; Xiao, K.; Liu, C. Efficient palladium-catalyzed C(sp2)–H activation towards the synthesis of fluorenes. New J. Chem., 2016, 40(11), 9030-9033.
[http://dx.doi.org/10.1039/C6NJ02033J]
[26]
Hwang, S.J.; Kim, H.J.; Chang, S. Highly efficient and versatile synthesis of polyarylfluorenes via Pd-catalyzed C-H bond activation. Org. Lett., 2009, 11(20), 4588-4591.
[http://dx.doi.org/10.1021/ol901854f] [PMID: 19754073]
[27]
Campeau, L.C.; Parisien, M.; Leblanc, M.; Fagnou, K. Biaryl synthesis via direct arylation: Establishment of an efficient catalyst for intramolecular processes. J. Am. Chem. Soc., 2004, 126(30), 9186-9187.
[http://dx.doi.org/10.1021/ja049017y] [PMID: 15281800]
[28]
Matute, M.B.; Mateo, C.; Cárdenas, D.J.; Echavarren, A.M. Intramolecular C-H activation by alkylpalladium(II) complexes: Insights into the mechanism of the palladium-catalyzed arylation reaction. Chem, 2001, 7(11), 2341-2348.
[http://dx.doi.org/10.1002/1521-3765(20010601)7:11<2341::AID-CHEM23410>3.0.CO;2-S] [PMID: 11446637]
[29]
Hagui, W.; Doucet, H.; Soulé, J.F. Application of palladium-catalyzed C(sp2)–H bond arylation to the synthesis of polycyclic (hetero)aromatics. Chem, 2019, 5(8), 2006-2078.
[http://dx.doi.org/10.1016/j.chempr.2019.06.005]
[30]
Dong, Z.; Wang, J.; Dong, G. Simple amine-directed meta-selective C–H arylation via Pd/norbornene catalysis. J. Am. Chem. Soc., 2015, 137(18), 5887-5890.
[http://dx.doi.org/10.1021/jacs.5b02809] [PMID: 25909445]
[31]
Vasu, D.; Yorimitsu, H.; Osuka, A. Palladium-assisted “aromatic metamorphosis” of dibenzothiophenes into triphenylenes. Angew. Chem. Int. Ed., 2015, 54(24), 7162-7166.
[http://dx.doi.org/10.1002/anie.201501992] [PMID: 25939804]
[32]
Chai, D.I.; Thansandote, P.; Lautens, M. Mechanistic studies of Pd-catalyzed regioselective aryl C-H bond functionalization with strained alkenes: Origin of regioselectivity. Chem, 2011, 17(29), 8175-8188.
[http://dx.doi.org/10.1002/chem.201100210] [PMID: 21647988]
[33]
Desai, L.V.; Stowers, K.J.; Sanford, M.S. Insights into directing group ability in palladium-catalyzed C-H bond functionalization. J. Am. Chem. Soc., 2008, 130(40), 13285-13293.
[http://dx.doi.org/10.1021/ja8045519] [PMID: 18781752]
[34]
Catellani, M.; Chiusoli, G.P. Palladacycle formation by electrophilic aromatic substitution, as monitored by 1H NMR spectroscopy. J. Organomet. Chem., 1992, 425(1-2), 151-154.
[http://dx.doi.org/10.1016/0022-328X(92)80031-R]
[35]
Larock, R.C.; Doty, M.J.; Tian, Q.; Zenner, J.M. Synthesis of polycyclic aromatic hydrocarbons by the Pd-catalyzed annulation of alkynes. J. Org. Chem., 1997, 62(22), 7536-7537.
[http://dx.doi.org/10.1021/jo9712557]
[36]
Alberico, D.; Scott, M.E.; Lautens, M. Aryl-aryl bond formation by transition-metal-catalyzed direct arylation. Chem. Rev., 2007, 107(1), 174-238.
[http://dx.doi.org/10.1021/cr0509760] [PMID: 17212475]
[37]
Shi, F.; Larock, R.C. Remote C–H Activation via through-space palladium and rhodium migrations.C-H Activation. Topics Current Chem; Yu, J.Q.; Shi, Z., Eds.; Springer: Berlin, Heidelberg, 2009, 292, pp. 123-64.
[http://dx.doi.org/10.1007/128_2008_46]
[38]
Phukon, J.; Gogoi, S. Palladium(II)-catalyzed vinylic geminal double C–H activation and alkyne annulation reaction: Synthesis of pentafulvenes. Chem. Commun., 2020, 56(7), 1133-1136.
[http://dx.doi.org/10.1039/C9CC09564K] [PMID: 31894770]
[39]
Qiao, S.; Deng, W.; Deng, G.; Liang, Y.; Yang, Y. Research advances in palladium-catalysed intermolecular C–H annulation of aryl halides with various aromatic ring precursors. Org. Biomol. Chem., 2022, 20(32), 6275-6292.
[http://dx.doi.org/10.1039/D2OB01129H] [PMID: 35861153]
[40]
Shi, Z.; Ding, S.; Cui, Y.; Jiao, N. A palladium-catalyzed oxidative cycloaromatization of biaryls with alkynes using molecular oxygen as the oxidant. Angew. Chem. Int. Ed., 2009, 48(42), 7895-7898.
[http://dx.doi.org/10.1002/anie.200903975] [PMID: 19739185]
[41]
Rice, J.E.; Cai, Z.W. A palladium-catalyzed intramolecular arene-triflate coupling for the synthesis of fluoranthenes and benzofluoranthenes. Tetrahedron Lett., 1992, 33(13), 1675-1678.
[http://dx.doi.org/10.1016/S0040-4039(00)91703-9]
[42]
Rice, J.E.; Cai, Z.W. An intramolecular arene-triflate coupling reaction for the regiospecific synthesis of substituted benzofluoranthenes. J. Org. Chem., 1993, 58(6), 1415-1424.
[http://dx.doi.org/10.1021/jo00058a023]
[43]
Smet, M.; Dijk, V.J.; Dehaen, W. An improved synthesis of substituted rubicenes providing access to heterocyclic rubicene analogues. Synlett, 1999, 1999(4), 495-497.
[http://dx.doi.org/10.1055/s-1999-2624]
[44]
Yamaguchi, M.; Higuchi, M.; Tazawa, K.; Manabe, K. Three-step synthesis of fluoranthenes through Pd-catalyzed inter- and intramolecular C–H arylation. J. Org. Chem., 2016, 81(9), 3967-3974.
[http://dx.doi.org/10.1021/acs.joc.6b00553] [PMID: 27045332]
[45]
Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Palladium‐catalyzed regioselective mono‐ and diarylation reactions of 2‐phenylphenols and naphthols with aryl halides. Angew. Chem. Int. Ed. Engl., 1997, 36(16), 1740-1742.
[http://dx.doi.org/10.1002/anie.199717401]
[46]
Müller, S.; Müllen, K. Facile synthetic approach to novel core-extended perylene carboximide dyes. Chem. Commun., 2005, (32), 4045-4046.
[http://dx.doi.org/10.1039/b509220e] [PMID: 16091794]
[47]
Chen, S.; Xiao, J.; Zhang, X.; Shen, X.; Liu, X.; Shen, F.; Yi, Y.; Song, Y. Effect of the mismatch structure on crystal packing, physical properties and third-order nonlinearity of unsymmetrical twistacenes. Dyes Pigments, 2016, 134, 9-18.
[http://dx.doi.org/10.1016/j.dyepig.2016.06.031]
[48]
Campo, M.A.; Larock, R.C. Novel 1,4-palladium migration in organopalladium intermediates derived from O-iodobiaryls. J. Am. Chem. Soc., 2002, 124(48), 14326-14327.
[http://dx.doi.org/10.1021/ja027548l] [PMID: 12452705]
[49]
Campo, M.A.; Huang, Q.; Yao, T.; Tian, Q.; Larock, R.C. 1,4-palladium migration via C-H activation, followed by arylation: Synthesis of fused polycycles. J. Am. Chem. Soc., 2003, 125(38), 11506-11507.
[http://dx.doi.org/10.1021/ja035121o] [PMID: 13129347]
[50]
Wegner, H.A.; Scott, L.T.; de Meijere, A. A new suzuki-heck-type coupling cascade: indeno[1,2,3]-annelation of polycyclic aromatic hydrocarbons. J. Org. Chem., 2003, 68(3), 883-887.
[http://dx.doi.org/10.1021/jo020367h] [PMID: 12558411]
[51]
Wegner, H.A.; Reisch, H.; Rauch, K.; Demeter, A.; Zachariasse, K.A.; de Meijere, A.; Scott, L.T. Oligoindenopyrenes: A new class of polycyclic aromatics. J. Org. Chem., 2006, 71(24), 9080-9087.
[http://dx.doi.org/10.1021/jo0613939] [PMID: 17109533]
[52]
González, J.J.; García, N.; Lor, G.B.; Echavarren, A.M. Synthesis of Spiro polycyclic aromatic hydrocarbons by intramolecular palladium-catalyzed arylation. J. Org. Chem., 1997, 62(5), 1286-1291.
[http://dx.doi.org/10.1021/jo962059n]
[53]
de Frutos, Ó.; Gómez-Lor, B.; Granier, T.; Monge, M.Á.; Puebla, G.E.; Echavarren, A.M. syn-Trialkylated truxenes: Building blocks that self-associate by arene stacking. Angew. Chem. Int. Ed., 1999, 38(1-2), 204-207.
[http://dx.doi.org/10.1002/(SICI)1521-3773(19990115)38:1/2<204::AID-ANIE204>3.0.CO;2-5]
[54]
Lor, G.B.; de Frutos, Ó.; Echavarren, A.M.; Lor, G.B. Synthesis of ‘crushed fullerene’ C60H30. Chem. Commun., 1999, (23), 2431-2432.
[http://dx.doi.org/10.1039/a906990i]
[55]
Lor, G.B. González-Cantala piedra, E.; Ruiz, M.; de Frutos, O.; Cárdenas, D. J.; Santos, A.; Echavarren, A. M. Synthesis of C3 benzo[1,2-e:3,4-e′:5,6-e′′]tribenzo[l]ace phenanthrylenes (“crushed fullerene” derivatives) by intramolecular palladium-catalyzed arylation. Chem, 2004, 10, 2601-2608.
[http://dx.doi.org/10.1002/chem.200306023] [PMID: 15146531]
[56]
Wang, L.; Shevlin, P.B. Formation of benzo[ghi]fluoranthenes by palladium catalyzed intramolecular coupling. Tetrahedron Lett., 2000, 41(3), 285-288.
[http://dx.doi.org/10.1016/S0040-4039(99)01940-1]
[57]
Wang, L.; Shevlin, P.B. Palladium-mediated Formation of Bowl-shaped PAHs: Synthesis of as -Indaceno[3,2,1,8,7,6,-p qrstuv]picenes. Org. Lett., 2000, 2(23), 3703-3705.
[http://dx.doi.org/10.1021/ol006611d] [PMID: 11073680]
[58]
Reisch, H.A.; Bratcher, M.S.; Scott, L.T. Imposing curvature on a polyarene by intramolecular palladium-catalyzed arylation reactions: A simple synthesis of Dibenzo. Org. Lett., 2000, 2(10), 1427-1430.
[http://dx.doi.org/10.1021/ol005755p] [PMID: 10814464]
[59]
Kim, D.; Petersen, J.L.; Wang, K.K. Synthesis of Bowl-shaped polycyclic aromatic hydrocarbons via palladium-catalyzed intramolecular arylation reactions. Org. Lett., 2006, 8(11), 2313-2316.
[http://dx.doi.org/10.1021/ol0605676]
[60]
Shi, X.; Roisnel, T.; Soulé, J.F.; Doucet, H. Synthesis of mono- and di-arylated acenaphthylenes and programmed access to dibenzo[ j, l]fluoranthenes via palladium-catalysed C–H bond functionalisation. Org. Chem. Front., 2018, 5(3), 398-408.
[http://dx.doi.org/10.1039/C7QO00799J]
[61]
Chaudhuri, R.; Hsu, M.Y.; Li, C.W.; Wang, C.I.; Chen, C.J.; Lai, C.K.; Chen, L.Y.; Liu, S.H.; Wu, C.C.; Liu, R.S. Functionalized dibenzo[g,p]chrysenes: Variable photophysical and electronic properties and liquid-crystal chemistry. Org. Lett., 2008, 10(14), 3053-3056.
[http://dx.doi.org/10.1021/ol801029x] [PMID: 18563905]
[62]
Li, C.W.; Wang, C.I.; Liao, H.Y.; Chaudhuri, R.; Liu, R.S. Synthesis of dibenzo[g,p]chrysenes from bis(biaryl)acetylenes via sequential ICl-induced cyclization and mizoroki−heck coupling. J. Org. Chem., 2007, 72(24), 9203-9207.
[http://dx.doi.org/10.1021/jo701504m] [PMID: 17973528]
[63]
Matsuoka, W.; Ito, H.; Itami, K. Rapid access to nanographenes and fused heteroaromatics by palladium‐catalyzed annulative π‐extension reaction of unfunctionalized aromatics with diiodobiaryls. Angew. Chem. Int. Ed., 2017, 56(40), 12224-12228.
[http://dx.doi.org/10.1002/anie.201707486] [PMID: 28800388]
[64]
Chen, T.A.; Liu, R.S. Synthesis of large polycyclic aromatic hydrocarbons from bis(biaryl)acetylenes: Large planar PAHs with low π-sextets. Org. Lett., 2011, 13(17), 4644-4647.
[http://dx.doi.org/10.1021/ol201854g] [PMID: 21827139]
[65]
Tsuji, H.; Ueda, Y.; Ilies, L.; Nakamura, E. Synthesis of tetrasubstituted alkenes by stereo- and regioselective stannyllithiation of diarylacetylenes. J. Am. Chem. Soc., 2010, 132(34), 11854-11855.
[http://dx.doi.org/10.1021/ja1059119] [PMID: 20698541]
[66]
Wu, X.; Han, J.; Wang, L.; Catalyzed, P.C-I. Palladium catalyzed C–I and vicinal C–H dual activation of diaryliodonium salts for diarylations: Synthesis of triphenylenes. J. Org. Chem., 2018, 83(1), 49-56.
[http://dx.doi.org/10.1021/acs.joc.7b01905] [PMID: 29171754]
[67]
Liu, Z.; Larock, R.C. Highly efficient route to fused polycyclic aromatics via palladium-catalyzed aryne annulation by aryl halides. J. Org. Chem., 2007, 72(1), 223-232.
[http://dx.doi.org/10.1021/jo0619534] [PMID: 17194103]
[68]
Kawasaki, S.; Satoh, T.; Miura, M.; Nomura, M. Synthesis of tetrasubstituted naphthalenes by palladium-catalyzed reaction of aryl iodides with internal alkynes. J. Org. Chem., 2003, 68(17), 6836-6838.
[http://dx.doi.org/10.1021/jo0346656] [PMID: 12919062]
[69]
Iwasaki, M.; Iino, S.; Nishihara, Y. Palladium-catalyzed annulation of o-iodobiphenyls with o-bromobenzyl alcohols: Synthesis of functionalized triphenylenes via C-C and C-H bond cleavages. Org. Lett., 2013, 15(20), 5326-5329.
[http://dx.doi.org/10.1021/ol4025869] [PMID: 24090170]
[70]
Iwasaki, M.; Araki, Y.; Iino, S.; Nishihara, Y. Synthesis of multisubstituted triphenylenes and phenanthrenes by cascade reaction of o -iodobiphenyls or (Z)-β-halostyrenes with o-bromobenzyl alcohols through two sequential C–C bond formations catalyzed by a palladium complex. J. Org. Chem., 2015, 80(18), 9247-9263.
[http://dx.doi.org/10.1021/acs.joc.5b01693] [PMID: 26322586]
[71]
Koga, Y.; Kaneda, T.; Saito, Y.; Murakami, K.; Itami, K. Synthesis of partially and fully fused polyaromatics by annulative chlorophenylene dimerization. Sci, 2018, 359(6374), 435-439.
[http://dx.doi.org/10.1126/science.aap9801] [PMID: 29371465]
[72]
Chang, N.; Chen, X.; Nonobe, H.; Okuda, Y.; Mori, H.; Nakajima, K.; Nishihara, Y. Synthesis of substituted picenes through Pd-catalyzed cross-coupling reaction/annulation sequences and their physicochemical properties. Org. Lett., 2013, 15(14), 3558-3561.
[http://dx.doi.org/10.1021/ol401375n] [PMID: 23815165]
[73]
Mori, H.; Chen, X.; Chang, N.; Hamao, S.; Kubozono, Y.; Nakajima, K.; Nishihara, Y. Synthesis of methoxy-substituted picenes: Substitution position effect on their electronic and single-crystal structures. J. Org. Chem., 2014, 79(11), 4973-4983.
[http://dx.doi.org/10.1021/jo500543h] [PMID: 24784450]
[74]
Chang, N.; Mori, H.; Chen, X.; Okuda, Y.; Okamoto, T.; Nishihara, Y. Synthesis of substituted [6]phenacenes through suzuki–miyaura coupling of polyhalobenzene with alkenylboronates and sequential intramolecular cyclization via C–H bond activation. Chem. Lett., 2013, 42(10), 1257-1259.
[http://dx.doi.org/10.1246/cl.130584]
[75]
Seifert, S.; Shoyama, K.; Schmidt, D.; Würthner, F. An electron‐poor C64 nanographene by palladium‐catalyzed cascade C−C bond formation: One‐pot synthesis and single‐crystal structure analysis. Angew. Chem. Int. Ed., 2016, 55(22), 6390-6395.
[http://dx.doi.org/10.1002/anie.201601433] [PMID: 27058998]
[76]
Kamikawa, K.; Takemoto, I.; Takemoto, S.; Matsuzaka, H. Synthesis of helicenes utilizing palladium-catalyzed double C-H arylation reaction. J. Org. Chem., 2007, 72(19), 7406-7408.
[http://dx.doi.org/10.1021/jo0711586] [PMID: 17705432]
[77]
Ruch, A.A.; Handa, S.; Kong, F.; Nesterov, V.N.; Pahls, D.R.; Cundari, T.R.; Slaughter, L.M. Competing amination and C–H arylation pathways in Pd/xantphos-catalyzed transformations of binaphthyl triflates: Switchable routes to chiral amines and helicene derivatives. Org. Biomol. Chem., 2016, 14(34), 8123-8140.
[http://dx.doi.org/10.1039/C6OB01102K] [PMID: 27507596]
[78]
Jiang, H.; Zhang, Y.; Chen, D.; Zhou, B.; Zhang, Y. An approach to tetraphenylenes via Pd-catalyzed C–H functionalization. Org. Lett., 2016, 18(9), 2032-2035.
[http://dx.doi.org/10.1021/acs.orglett.6b00641] [PMID: 27109585]
[79]
Fu, W.C.; Kwong, F.Y. A denitrogenative palladium-catalyzed cascade for regioselective synthesis of fluorenes. Chem. Sci., 2020, 11(5), 1411-1417.
[http://dx.doi.org/10.1039/C9SC04062E] [PMID: 34123265]
[80]
Pigulski, B.; Ximenis, M.; Shoyama, K.; Würthner, F. Synthesis of polycyclic aromatic hydrocarbons by palladium-catalysed [3 + 3] annulation. Org. Chem. Front., 2020, 7(19), 2925-2930.
[http://dx.doi.org/10.1039/D0QO00968G]
[81]
Jana, R.; Chatterjee, I.; Samanta, S.; Ray, J.K. Novel and rapid palladium-assisted 6π electrocyclic reaction affording 9,10-dihydrophenanthrene and its analogues. Org. Lett., 2008, 10(21), 4795-4797.
[http://dx.doi.org/10.1021/ol801882t] [PMID: 18828592]
[82]
Lan, Y.; Wang, C.; Sowa, J.R., Jr; Wu, Y.D. A theoretical investigation on the mechanism of a palladium-mediated formal 6π electrocyclic synthesis of 9,10-dihydrophenanthrenes. J. Org. Chem., 2010, 75(3), 951-954.
[http://dx.doi.org/10.1021/jo902163v] [PMID: 20039689]
[83]
Park, H.; Yoo, K.; Jung, B.; Kim, M. Direct synthesis of anthracenes from O-tolualdehydes and aryl iodides through Pd(II)-Catalyzed sp C H arylation and electrophilic aromatic cyclization. Tetrahedron, 2018, 74(16), 2048-2055.
[http://dx.doi.org/10.1016/j.tet.2018.03.006]
[84]
Tang, M.; Yu, Q.; Wang, Z.; Zhang, C.; Sun, B.; Yi, Y.; Zhang, F.L. Synthesis of polycyclic aromatic hydrocarbons (PAHs) via a transient directing group. Org. Lett., 2018, 20(23), 7620-7623.
[http://dx.doi.org/10.1021/acs.orglett.8b03359] [PMID: 30457344]
[85]
Scott, L.T. Fragments of fullerenes: Novel syntheses, structures and reactions. Pure Appl. Chem., 1996, 68(2), 291-300.
[http://dx.doi.org/10.1351/pac199668020291]
[86]
Wu, Y.T.; Linden, A.; Siegel, J.S. Formal [(2+2)+2] and [(2+2)+(2+2)] nonconjugated dienediyne cascade cycloadditions. Org. Lett., 2005, 7(20), 4353-4355.
[http://dx.doi.org/10.1021/ol0514799] [PMID: 16178531]
[87]
Marcinow, Z.; Sygula, A.; Ellern, A.; Rabideau, P.W. Lowering inversion barriers of buckybowls by benzannelation of the rim: Synthesis and crystal and molecular structure of 1,2-dihydrocyclopenta[b,c]dibenzo[g,m] corannulene. Org. Lett., 2001, 3(22), 3527-3529.
[http://dx.doi.org/10.1021/ol016607h] [PMID: 11678699]
[88]
Shi, K.; Lei, T.; Wang, X.Y.; Wang, J.Y.; Pei, J. A bowl-shaped molecule for organic field-effect transistors: Crystal engineering and charge transport switching by oxygen doping. Chem. Sci., 2014, 5(3), 1041-1045.
[http://dx.doi.org/10.1039/C3SC52701H]
[89]
Liu, Z.; Larock, R.C. Palladium-catalyzed, sequential, three-component cross-coupling of aryl halides, alkynes, and arynes. Angew. Chem. Int. Ed., 2007, 46(14), 2535-2538.
[http://dx.doi.org/10.1002/anie.200604969] [PMID: 17328028]
[90]
Wang, C.; Rakshit, S.; Glorius, F. Palladium-catalyzed intermolecular decarboxylative coupling of 2-phenylbenzoic acids with alkynes via C-H and C-C bond activation. J. Am. Chem. Soc., 2010, 132(40), 14006-14008.
[http://dx.doi.org/10.1021/ja106130r] [PMID: 20831188]
[91]
Yang, X.; Chen, X.; Xu, Y.; Zhang, M.; Deng, G.; Yang, Y.; Liang, Y. Palladium-catalyzed [4 + 3] or [2 + 2 + 3] annulation via C–H activation and subsequent decarboxylation: Access to heptagon-embedded polycyclic aromatic hydrocarbons. Org. Lett., 2021, 23(7), 2610-2615.
[http://dx.doi.org/10.1021/acs.orglett.1c00520] [PMID: 33729805]
[92]
Fu, W.C.; Wang, Z.; Chan, W.T.K.; Lin, Z.; Kwong, F.Y. Regioselective synthesis of polycyclic and heptagon‐embedded aromatic compounds through a versatile π‐extension of aryl halides. Angew. Chem. Int. Ed., 2017, 56(25), 7166-7170.
[http://dx.doi.org/10.1002/anie.201703551] [PMID: 28510348]
[93]
Zhao, Q.; Fu, W.C.; Kwong, F.Y. Palladium‐catalyzed regioselective aromatic extension of internal alkynes through a norbornene‐controlled reaction sequence. Angew. Chem. Int. Ed., 2018, 57(13), 3381-3385.
[http://dx.doi.org/10.1002/anie.201713207] [PMID: 29385308]
[94]
Yang, Y.; Zhou, L.; Yang, X.; Luo, X.; Deng, G.; Yang, Y.; Liang, Y. Synthesis of phenanthrenes via palladium-catalyzed three-component domino reaction of aryl iodides, internal alkynes, and o-bromobenzoic acids. Synthesis, 2020, 52(8), 1223-1230.
[http://dx.doi.org/10.1055/s-0039-1690737]
[95]
Yang, Y.; Zhou, B.; Zhu, X.; Deng, G.; Liang, Y.; Yang, Y. Palladium-catalyzed synthesis of triphenylenes via sequential C–H activation and decarboxylation. Org. Lett., 2018, 20(17), 5402-5405.
[http://dx.doi.org/10.1021/acs.orglett.8b02310] [PMID: 30132677]
[96]
Zhou, L.; Sun, M.; Zhou, F.; Deng, G.; Yang, Y.; Liang, Y. Atmosphere-controlled palladium-catalyzed divergent decarboxylative cyclization of 2-iodobiphenyls and α-oxocarboxylic acids. Org. Lett., 2021, 23(18), 7150-7155.
[http://dx.doi.org/10.1021/acs.orglett.1c02559] [PMID: 34463519]

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