Login Register Cart 0
Generic placeholder image

Mini-Reviews in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-193X
ISSN (Online): 1875-6298

Back
Journal Home About Journal Editorial Board Journal Insight Current Issue Volumes/Issues
Subscribe
Mini-Review Article

Recent Advances in the Cross-Coupling of Arylaluminums with Electrophile Reagents

Author(s): Li Qinghan*, Jiang Xin, Wu Kun, Luo Ruiqiang, Zhang Zhihao, Liang Meng and Huang Zheyao

Volume 18, Issue 2, 2021

Published on: 23 July, 2020

Page: [213 - 220] Pages: 8

DOI: 10.2174/1570193X17999200723160453

Price: $65

Abstract

The arylaluminum reagents are good nucleophiles for organic reactions because of their high reactivity, high chemoselective, low toxicity, and ease of preparation. Therefore, arylaluminum reagents are widely applied in many organic reactions. This review summarizes the recent advancement of the arylaluminum reagents applied in cross-coupling reactions, involving various reaction systems and properties of reaction.

Keywords: Arylaluminum reagents, C-C/N bond formation, cross-coupling reaction, electrophiles reagents, organic synthesis, research progress.

« Previous Next »
Graphical Abstract

[1]
Woodward, S.; Dagorne, S. Topics in Organometallic Chemistry; Woodward, S; Dagorne, S., Ed.; Springer: Berlin, 2013, Vol. 41, pp. 1-312.
Knochel, P.; Blümke, T.; Groll, K.; Chen, Y-H. Preparation of Organoalanes for Organic Synthesis.Topics in Organometallic Chemistry; Woodward, S.; Dagorne, S., Eds.; Springer: Berlin, 2013, Vol. 41, pp. 173-186.
Kolb, A.; Zezschwitz, P. Organoaluminum couplings to carbonyls, imines, and halides.Topics in Organometallic Chemistry; Woodward, S.; Dagorne, S., Eds.; Springer: Berlin, 2013, Vol. 41, pp. 245-276.
[2]
Li, Q.H.; Shao, X.B.; Ding, Y.; Wen, C.; Zhao, Z.G. Research progress on cross-coupling reactions of alkenylaluminum with electrophilic reagents. Curr. Org. Chem., 2018, 22, 1523-1535.
[http://dx.doi.org/10.2174/1385272822666180704143509]
[3]
Li, Q.H.; Wang, J.H.; Wen, C.; Xin, J.; Cao, K.P.; Wu, K.; Liang, M. Research progress on cross-coupling reactions of alkynylaluminum with electrophiles reagents. Chin. Chem. Lett., 2019.
[http://dx.doi.org/10.1016/j.cclet.2019.02.028.]
[4]
Maruoka, K.; Yamamoto, H. Tetrahedron report number 239: Organoaluminums in organic synthesis. Tetrahedron, 1988, 44, 5001-5032.
[http://dx.doi.org/10.1016/S0040-4020(01)86007-5]
[5]
Wang, C.; Xi, Z. Co-operative effect of Lewis acids with transition metals for organic synthesis. Chem. Soc. Rev., 2007, 36(9), 1395-1406.
[http://dx.doi.org/10.1039/b608694m] [PMID: 17660873]
[6]
Uhl, W. Hydroalumination and hydrogallation of alkynes: New insights into the course of well-known reactions. Coord. Chem. Rev., 2008, 252, 1540-1563.
[http://dx.doi.org/10.1016/j.ccr.2008.01.026]
[7]
Ruiz-Castillo, P.; Buchwald, S.L. Applications of palladium-catalyzed C-N cross-coupling reactions. Chem. Rev., 2016, 116(19), 12564-12649.
[http://dx.doi.org/10.1021/acs.chemrev.6b00512] [PMID: 27689804]
[8]
Johnson, J.B.; Rovis, T. More than bystanders: The effect of olefins on transition-metal-catalyzed cross-coupling reactions. Angew. Chem. Int. Ed. Engl., 2008, 47(5), 840-871.
[http://dx.doi.org/10.1002/anie.200700278] [PMID: 18081111]
[9]
Magano, J.; Monfette, S. Development of an air-stable, broadly applicable nickel source for nickel-catalyzed cross-coupling. ACS Catal., 2015, 5, 3120-3123.
[http://dx.doi.org/10.1021/acscatal.5b00498]
[10]
Tucker, C.E. Vries, de J. G. Homogeneous catalysis for the production of fine chemicals. Palladium- and nickel-catalysed aromatic carbon-carbon bond formation. Top. Catal., 2002, 19, 111-118.
[http://dx.doi.org/10.1023/A:1013841518270]
[11]
Hornillos, V.; Pérez, M.; Fañanás-Mastral, M.; Feringa, B.L. Copper-catalyzed enantioselective allyl-allyl cross-coupling. J. Am. Chem. Soc., 2013, 135(6), 2140-2143.
[http://dx.doi.org/10.1021/ja312487r] [PMID: 23350620]
[12]
Ding, S.Y.; Xu, L.; Li, P.F. Copper-catalyzed boron-selective C(sp2)-C(sp3) oxidative cross-coupling of arylboronic acids and alkyltrifluoro borates involving a single-electron transmetalation process. ACS Catal., 2016, 6, 1329-1333.
[http://dx.doi.org/10.1021/acscatal.5b02524]
[13]
Li, Q.H.; Shao, X.B.; Zhang, G.; Ding, Y.; Yang, X.J.; Chen, F. Recent advance of palladium-catalyzed cross-coupling reactions of organoalanes with electrophiles reagents. Youji Huaxue, 2018, 38, 802-811.
[http://dx.doi.org/10.6023/cjoc201709041]
[14]
Shao, X.B.; Jiang, X.; Li, Q.H.; Zhao, Z.G. Highly efficient synthesis of 1,2-disubstituted acetylenes derivatives from the cross-coupling reactions of 1-bromoalkynes with organoalane reagents. Tetrahedron, 2018, 74, 6063-6070.
[http://dx.doi.org/10.1016/j.tet.2018.08.050]
[15]
Chen, B.; Wu, X.F. Palladium-catalyzed synthesis of 1,2-diketones from aryl halides and organoaluminum reagents uing tert-butyl isocyanide as the CO source. Org. Lett., 2020, 22(2), 636-641.
[http://dx.doi.org/10.1021/acs.orglett.9b04414] [PMID: 31908172]
[16]
Greene, M.A.; Yonova, I.M.; Williams, F.J.; Jarvo, E.R. Traceless directing group for stereospecific nickel-catalyzed alkyl-alkyl cross-coupling reactions. Org. Lett., 2012, 14(16), 4293-4296.
[http://dx.doi.org/10.1021/ol300891k] [PMID: 22568515]
[17]
Tarui, A.; Shinohara, S.; Sato, K.; Omote, M.; Ando, A. Nickel-catalyzed Negishi cross-coupling of bromodifluoroacetamides. Org. Lett., 2016, 18(5), 1128-1131.
[http://dx.doi.org/10.1021/acs.orglett.6b00232] [PMID: 26910536]
[18]
Ogawa, H.; Yang, Z.K.; Minami, H.; Kojima, K.; Saito, T.; Wang, C.; Uchiyama, M. Revisit of organoaluminum reagents affords a versatile protocol for C-X (X = N, O, F) bond-cleavage cross-coupling: A systematic study. ACS Catal., 2017, 7, 3988-3994.
[http://dx.doi.org/10.1021/acscatal.7b01058]
[19]
Liu, C.Y.; Wititsuwannakul, T.; Hsieh, C.H.; Tsai, C.Y.; Wang, T.H.; Ambre, R.; Chen, W.C.; Surawatanawong, P.; Ong, T.G. Nickel- mediated cross-coupling via C-O activation assisted by organoaluminum. J. Chin. Chem. Soc. (Taipei), 2020, 67, 376-382.
[20]
Naganawa, Y.; Guo, H.Q.; Sakamoto, K.; Nakajima, Y. Nickel- catalyzed selective cross-coupling of chlorosilanes with organo aluminum reagents. ChemCatChem, 2019, 11, 3756-3759.
[http://dx.doi.org/10.1002/cctc.201900047]
[21]
Santandrea, J.; Bédard, A.C.; Collins, S.K. Cu(I)-catalyzed macrocyclic Sonogashira-type cross-coupling. Org. Lett., 2014, 16(15), 3892-3895.
[http://dx.doi.org/10.1021/ol501898b] [PMID: 25054848]
[22]
Maaliki, C.; Thiery, E.; Thibonne, J. Emergence of copper-mediated formation of C-C bonds. Eur. J. Org. Chem., 2017, 2, 209-228.
[http://dx.doi.org/10.1002/ejoc.201600540]
[23]
Wunderlich, S.H.; Knochel, P. Aluminum bases for the highly chemoselective preparation of aryl and heteroaryl aluminum compounds. Angew. Chem. Int. Ed. Engl., 2009, 48(8), 1501-1504.
[http://dx.doi.org/10.1002/anie.200804966] [PMID: 19142920]
[24]
Blümke, T.D.; Groll, K.; Karaghiosoff, K.; Knochel, P. New preparation of benzylic aluminum and zinc organometallics by direct insertion of aluminum powder. Org. Lett., 2011, 13(24), 6440-6443.
[http://dx.doi.org/10.1021/ol202733v] [PMID: 22098566]
[25]
Klatt, T.; Groll, K.; Knochel, P. Generation of functionalized aryl and heteroaryl aluminum reagents by halogen-lithium exchange. Chem. Commun. (Camb.), 2013, 49(62), 6953-6955.
[http://dx.doi.org/10.1039/c3cc43356k] [PMID: 23802222]
[26]
Zhou, S.; Yang, Z.; Chen, X.; Li, Y.; Zhang, L.; Fang, H.; Wang, W.; Zhu, X.; Wang, S. Copper-catalyzed electrophilic amination of organoaluminum nucleophiles with O-benzoyl hydroxylamines. J. Org. Chem., 2015, 80(12), 6323-6328.
[http://dx.doi.org/10.1021/acs.joc.5b00767] [PMID: 26030723]
[27]
Yoon, H.; Lee, Y. Copper-catalyzed electrophilic amination of heteroarenes via C-H alumination. J. Org. Chem., 2015, 80(20), 10244-10251.
[http://dx.doi.org/10.1021/acs.joc.5b01863] [PMID: 26421609]
[28]
Parchomyk, T.; Koszinowski, K. Iron-catalyzed cross-coupling: Mechanistic insight for rational applications in synthesis. Synthesis, 2017, 15, 3269-3280.
[http://dx.doi.org/10.1055/s-0036-1588428]
[29]
Shi, J.L.; Zhang, J.C.; Wang, B.Q.; Hu, P.; Zhao, K.Q.; Shi, Z.J. Fe-promoted chlorobenzylation of terminal alkynes through benzylic C(sp3)-H bond functionalization. Org. Lett., 2016, 18(6), 1238-1241.
[http://dx.doi.org/10.1021/acs.orglett.5b02472] [PMID: 26950017]
[30]
Czaplik, W.M.; Mayer, M.; Cvengroš, J.; von Wangelin, A.J. Coming of age: Sustainable iron-catalyzed cross-coupling reactions. ChemSusChem, 2009, 2(5), 396-417.
[http://dx.doi.org/10.1002/cssc.200900055] [PMID: 19425040]
[31]
Kawamura, S.; Agata, R.; Nakamura, M. Regio- and stereoselective multi-substituted olefin synthesis via hydro/carboalumination of alkynes and subsequent iron-catalysed cross-coupling reaction with alkyl halides. Org. Chem. Front., 2015, 2, 1053-1058.
[http://dx.doi.org/10.1039/C5QO00147A]
[32]
Kawamura, S.; Ishizuka, K.; Takaya, H.; Nakamura, M. The first iron-catalysed aluminium-variant Negishi coupling: Critical effect of co-existing salts on the dynamic equilibrium of arylaluminium species and their reactivity. Chem. Commun. (Camb.), 2010, 46(33), 6054-6056.
[http://dx.doi.org/10.1039/c0cc01216e] [PMID: 20657915]
[33]
Fagnou, K.; Lautens, M. Rhodium-catalyzed carbon-carbon bond forming reactions of organometallic compounds. Chem. Rev., 2003, 103(1), 169-196.
[http://dx.doi.org/10.1021/cr020007u] [PMID: 12517183]
[34]
Colby, D.A.; Bergman, R.G.; Ellman, J.A. Rhodium-catalyzed C-C bond formation via heteroatom-directed C-H bond activation. Chem. Rev., 2010, 110(2), 624-655.
[http://dx.doi.org/10.1021/cr900005n] [PMID: 19438203]
[35]
Tanaka, S.; Mori, A. Rhodium-catalyzed cross-coupling of vinylarenes with arylaluminum reagents in the presence of ketones. Eur. J. Org. Chem., 2014, 6, 1167-1171.
[http://dx.doi.org/10.1002/ejoc.201301757]
[36]
Tanaka, S.; Itami, K.; Sunahara, K.; Tatsuta, G.; Mori, A. Ethylaluminum as an ethylene source for the Mizoroki-Heck-type reaction. Rhodium-catalyzed preparation of stilbene derivatives. Chem. Commun. (Camb.), 2015, 51(10), 1949-1952.
[http://dx.doi.org/10.1039/C4CC09306B] [PMID: 25531729]
[37]
Ishikawa, T.; Ogawa, A.; Hirao, T. A novel oxovanadium(V)-induced oxidation of organoaluminum compounds. Highly selective coupling of organic substituents on aluminum. J. Am. Chem. Soc., 1998, 120, 5124-5125.
[http://dx.doi.org/10.1021/ja973891s]
[38]
Miyoshi, T.; Miyakawa, T.; Ueda, M.; Miyata, O. Nucleophilic α-arylation and α-alkylation of ketones by polarity inversion of N-alkoxyenamines: Entry to the umpolung reaction at the α-carbon position of carbonyl compounds. Angew. Chem. Int. Ed. Engl., 2011, 50(4), 928-931.
[http://dx.doi.org/10.1002/anie.201004374] [PMID: 21246693]
[39]
Minami, H.; Saito, T.; Wang, C.; Uchiyama, M. Organoaluminum-mediated direct cross-coupling reactions. Angew. Chem. Int. Ed. Engl., 2015, 54(15), 4665-4668.
[http://dx.doi.org/10.1002/anie.201412249] [PMID: 25704076]

Rights & Permissions Print Cite
Article Metrics
19
1
© 2024 Bentham Science Publishers | Privacy Policy