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Current Organic Chemistry

Editor-in-Chief

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

Recent Applications of Aryltriazenes in Organic Synthesis via C-N/N-N Bond Cleavage

Author(s): Yonghong Zhang, Dawei Cao, Wenbo Liu, Haiyan Hu, Xiaomei Zhang and Chenjiang Liu

Volume 19, Issue 2, 2015

Page: [151 - 178] Pages: 28

DOI: 10.2174/1385272819666150119222344

Price: $65

Abstract

Aryltriazenes have emerged as highly powerful and versatile building blocks in a variety of synthetic transformations, which attracted extensive attentions due to their advantages of good reactivity, well stability, ready availability, operational simplicity and diverse transformation. In this review, we summarize the current progresses involving aryltriazenes as starting materials or active intermediates for various synthetically useful applications via C-N/N-N bond cleavage.

Keywords: Aryltriazenes, Carbon-Carbon/Hetero-atom Bond Formation, C-N/N-N Bond Cleavage, Organic Synthesis.

Graphical Abstract

[1]
Griess, P. Ueber eine neue klasse organischer verbindungen, in denen wasserstoff durch stickstoff vertreten ist. Justus Liebigs Ann. Chem., 1862, 121, 257-280.
[2]
Baeyer, A.; Jaeger, C. Ueber die Amide des Diazobenzols. Ber. Dtsch. Chem. Ges., 1875, 8, 148-151.
[3]
Rouzer, C.A.; Sabourin, M.; Skinner, T.L.; Thompson, E.J.; Wood, T.O.; Chmurny, G.N.; Klose, J.R.; Roman, J.M.; Smith, R.H., Jr; Michejda, C.J. Oxidative metabolism of 1-(2-chloroethyl)-3-alkyl-3-(methylcarbamoyl)tri-azenes: Formation of chloroacetaldehyde and relevance to biological activity. Chem. Res. Toxicol., 1996, 9, 172-178.
[4]
Connors, T.A.; Goddard, P.M.; Merai, K.; Ross, W.C.J.; Wilman, D.E.V. Tumor inhibitory triazenes: Structural requirements for an active metabolite. Biochem. Pharmacol., 1976, 25, 241-246.
[5]
Nicolaou, K.C.; Boddy, C.N.C.; Li, H.; Koumbis, A.E.; Hughes, R.; Natarajan, S.; Jain, N.F.; Ramanjulu, J.M.; Bräse, S.; Solomon, M.E. Total synthesis of vancomycin-part 2: Retrosynthetic analysis, synthesis of amino acid building blocks and strategy evaluations. Chem. Eur. J., 1999, 5, 2602-2621.
[6]
Moore, J.S. Shape-persistent molecular architectures of nanoscale dimension. Acc. Chem. Res., 1997, 30, 402-413.
[7]
Kimball, D.B.; Haley, M.M. Triazenes: A versatile tool in organic synthesis. Angew. Chem. Int. Ed., 2002, 41, 3338-3351.
[8]
Brase, S.; Dahmen, S.; Pfefferkorn, M. Solid-phase synthesis of urea and amide libraries using the T2 triazene linker. J. Comb. Chem., 2000, 2, 710-715.
[9]
Braese, S.; Muller, T. Aryltriazenes, aryltetrazenes, and related compounds.In: Science of Synthesis: Houben-Weyl Methods of Molecular Transformations; Georg Thieme Verlag: Stuttgart, Germany, 2007, Vol. 31b, pp. 1845-1872.
[10]
Khramov, D.M.; Bielawski, C.W. Donor-acceptor triazenes: Synthesis, characterization, and study of their electronic and thermal properties. J. Org. Chem., 2007, 72, 9407-9417.
[11]
Sieh, D.H.; Wilbur, D.J.; Michejda, C.J. Preparation of trialkyltriazenes. A comparison of the nitrogen-nitrogen bond rotation in trialkyltriazenes and aryldialkyltriazenes by variable temperature 13C NMR. J. Am. Chem. Soc., 1980, 102, 3883-3887.
[12]
Damschroder, R.E.; Peterson, W.D. 1,2,3-Benzotriazole.Organic Syntheses; John Wiley & Sons, Inc., 2003.
[13]
Bhattacharya, S.; Majee, S.; Mukherjee, R.; Sengupta, S. Heck reaction of 1-aryltriazenes. Synth. Commun., 1995, 25, 651-657.
[14]
Sengupta, S.; Sadhukkan, S.K. Iodoarenediazonium salts: A new class of aromatic substrates for differential palladium catalyzed reactions. Tetrahedron Lett., 1998, 39, 715-718.
[15]
Sengupta, S.; Sadhukkan, S.K. Synthesis of symmetrical trans-stilbenes by a double Heck reaction of (arylazo)amines with vinyltriethoxysilane: trans-4,4′-dibromostilbene. Org. Synth., 2002, 79, 52-58.
[16]
Bräse, S.; Schroen, M. Efficient cleavage-cross-coupling strategy for solid-phase synthesis- a modular building system for combinatorial chemistry. Angew. Chem. Int. Ed., 1999, 38, 1071-1073.
[17]
Saeki, T.; Son, E.C.; Tamao, K. Boron trifluoride induced palladium-catalyzed cross-coupling reaction of 1-aryltriazenes with areneboronic acids. Org. Lett., 2004, 6, 617-619.
[18]
Liu, C.Y.; Gavryushin, A.; Knochel, P. Synthesis of functionalized o-, m-, and p-terphenyl derivatives by consecutive cross-coupling reactions of triazene-substituted arylboronic esters. Chem. Asian J., 2007, 2, 1020-1030.
[19]
Nan, G.M.; Ren, F.; Luo, M.M. Suzuki-Miyaura cross-coupling reaction of 1-aryl-triazenes with arylboronic acids catalyzed by a recyclable polymer-supported N-heterocyclic carbene-palladium complex catalyst. Beilstein J. Org. Chem., 2010, 6, 1-6.
[20]
Nan, G.M.; Zhu, F.H.; Wei, Z.J. Ligand-free Suzuki-Miyaura cross-coupling reactions of aryl-triazenes with arylboronic acids. Chin. J. Chem., 2011, 29, 72-78.
[21]
Saeki, T.; Matsunaga, T.; Son, E.C.; Tamao, K. Palladium-catalyzed cross-coupling reaction of 1-aryltriazenes with aryl- and alkenyltrifluorosilanes. Adv. Synth. Catal., 2004, 346, 1689-1692.
[22]
Nan, G.; Zhou, J. Study on Lewis acid induced the stille cross-coupling reactions of aryltriazenes as substrates. Chin. J. Org. Chem, 2012, 32, 1695-1699.
[23]
Wang, R.; Falck, J.R. Room temperature, open-flask C-H arylation of electron-deficient heteroarenes with triazenes: Rapid synthesis of heterobiaryls. Org. Chem. Front., 2014, 1, 1029-1034.
[24]
Hafner, A.; Bräse, S. Ortho-trifluoromethylation of functionalized aromatic triazenes. Angew. Chem. Int. Ed., 2012, 51, 3713-3715.
[25]
Hafner, A.; Bräse, S. Trifluoromethylation of 1-aryl-3,3-diisopropyltriazenes. Adv. Synth. Catal., 2013, 355, 996-1000.
[26]
Hafner, A.; Hussal, C.; Bräse, S. Preparation of aromatic triazenes and their application in silver-mediated perfluoroalkylation reactions. Synthesis, 2014, 46, 1448-1454.
[27]
Patrick, T.B.; Juehne, T.; Reeb, E.; Hennessy, D. Zinc(II) promoted conversion of aryltriazenes to aryl iodides and aryl nitriles. Tetrahedron Lett., 2001, 42, 3553-3554.
[28]
Zhu, C.; Yamane, M. Transition-metal-free borylation of aryltriazene mediated by BF3OEt2. Org. Lett., 2012, 14, 4560-4563.
[29]
Foster, N.I.; Heindel, N.D.; Burns, N.D.; Muhr, W. Aryl iodides from anilines via triazene intermediates. Synthesis, 1980, 1980, 572-573.
[30]
Ku, H.; Barrio, J.R. Convenient synthesis of aryl halides from arylamines via treatment of l-aryl-3,3-dialkyltriazenes with trimethylsilyl halides. J. Org. Chem., 1981, 46, 5239-5241.
[31]
Ponchant, M.; Dreux, Y.; Kamenka, J.M.; Chicheportiche, R.; Beaucourt, J.P. Synthesis of 3-[125I]-iodo-phencyclidine for biological studies. J. Labelled Comp. Radiopharm., 1990, 18, 1059-1064.
[32]
Wu, Z.Y.; Moore, J.S. Iodine-promoted decomposition of 1-aryl-3,3-dialkyltriazenes: A mild method for the synthesis of aryl iodides. Tetrahedron Lett., 1994, 35, 5539-5542.
[33]
Balz, G.; Schiemann, G. Über Aromatische fluorverbindungen, i.: Ein neues verfahren zu ihrer darstellung. Ber. Dtsch. Chem. Ges., 1927, 60, 1186-1190.
[34]
Rosenfeld, M.N.; Widdowson, D.A. A mild and efficient method of aromatic fluorination J. Chem. Soc., Chem. Comm, 1979, 914-916.
[35]
Satyamurthy, N.; Barrio, J.R.; Schmidt, D.G.; Kammerer, C.; Bida, G.T.; Phelps, M.E. Acid-catalyzed thermal decomposition of 1-aryl-3,3-dialkyltriazenes in the presence of nucleophiles. J. Org. Chem., 1990, 55, 4560-4564.
[36]
Döbele, M.; Vanderheiden, S.; Jung, N.; Bräse, S. Synthesis of aryl fluorides on a solid support and in solution by utilizing a fluorinated solvent. Angew. Chem. Int. Ed., 2010, 49, 5986-5988.
[37]
Lormann, M.; Dahmen, S.; Bräse, S. Hydro-dediazoniation of diazonium salts using trichlorosilane: New cleavage conditions for the T1 traceless linker. Tetrahedron Lett., 2000, 41, 3813-3816.
[38]
Kovac, M.; Anderluh, M.; Vercouillie, J.; Guilloteau, D.; Emond, P.; Mavel, S. Aromatic fluoro-de-triazenation with boron trifluoride diethyl etherate under non-protic acid conditions. J. Fluor. Chem., 2013, 147, 5-9.
[39]
Li, Q.; Jin, C.S.; Petukhov, P.A.; Rukavishnikov, A.V.; Zaikova, T.O.; Phadke, A.; LaMunyon, D.H.; Lee, M.D.; Keana, J.F.W. Synthesis of well-defined tower-shaped 1,3,5-trisubstituted adamantanes incorporating a macrocyclic trilactam ring system. J. Org. Chem., 2004, 69, 1010-1019.
[40]
Romanato, P.; Duttwyler, S.; Linden, A.; Baldridge, K.K.; Siegel, J.S. Intramolecular halogen stabilization of silylium ions directs gearing dynamics. J. Am. Chem. Soc., 2010, 132, 7828-7829.
[41]
Jenny, N.M.; Wang, H.; Neuburger, M.; Fuchs, H.; Chi, L.F.; Mayor, M. Synthesis and solid-state investigations of oligo-phenylene-ethynylene structures with halide end-groups. Eur. J. Org. Chem., 2012, 2012, 2738-2747.
[42]
Romanato, P.; Duttwyler, S.; Linden, A.; Baldridge, K.K.; Siegel, J.S. Competition between π-arene and lone-pair halogen coordination of silylium ions? J. Am. Chem. Soc., 2011, 133, 11844-11846.
[43]
Kirk, M.L.; Shultz, D.A.; Stasiw, D.E.; Lewis, G.F.; Wang, G.B.; Brannen, B.L.; Sommer, R.D.; Boyle, P.D. Superexchange contributions to distance dependence of electron transfer/transport: Exchange and electronic coupling in oligo(para-phenylene)- and oligo(2,5-thiophene)-bridged donor-bridge-acceptor biradical complexes. J. Am. Chem. Soc., 2013, 135, 17144-17154.
[44]
Romanato, P.; Duttwyler, S.; Linden, A.; Baldridge, K.K.; Siegel, J.S. Through-space interactions in enshrouded m-terphenylsilanes. J. Phys. Org. Chem., 2014, 27, 277-283.
[45]
Liu, C.Y.; Knochel, P. Preparation of polyfunctional aryl azides from aryl triazenes. A new synthesis of ellipticine, 9-methoxyellipticine, isoellipticine, and 7- carbethoxyisoellipticine. J. Org. Chem., 2007, 72, 7106-7115.
[46]
Yang, W.J.; Xu, L.J.; Chen, Z.K.; Zhang, L.L.; Miao, M.Z.; Ren, H.J. Ru-catalyzed synthesis of dihydrofuroquinolines from azido-cyclopropyl ketones. Org. Lett., 2013, 15, 1282-1285.
[47]
Lunn, G.; Sansone, E.B.; Keefer, L.K. General cleavage of N-N and N-O bonds using nickel/aluminum alloy. Synthesis, 1985, 1985, 1104-1108.
[48]
Mori, S.; Aoyama, T.; Shioiri, T. New methods and reagents in organic synthesis. 60. A new synthesis of aromatic and heteroaromatic amines using diphenyl phosphorazidate (DPPA). Chem. Pharm. Bull. (Tokyo), 1986, 34, 1524-1530.
[49]
Trost, B.M.; Pearson, W.H. Azidomethyl phenyl sulfide. A synthon for NH2. J. Am. Chem. Soc., 1981, 103, 2483-2485.
[50]
Avemaria, F.; Zimmermann, V.; Bräse, S. Synthesis of aryl azides via post-cleavage modification of polymer-bound triazenes. Synlett, 2004, 2004, 1163-1166.
[51]
Barek, J.; Kubickova, J.; Mejstrik, V.; Zuna, J. The polarographic and voltammetric determination of 1-(3′-carbamoylphenyl)-3,3-mimethyltriazene. Collect. Czech. Chem. Commun., 1992, 57, 2263-2271.
[52]
Liu, C.; Lv, J.; Luo, S.; Cheng, J.P. Sc(OTf)3-catalyzed transfer diazenylation of 1,3-dicarbonyls with triazenes via N-N bond cleavage. Org. Lett., 2014, 16, 5458-5461.
[53]
Khazaei, A.; Kazem-Rostami, M.; Moosavi-Zare, A.R.; Bayat, M.; Saednia, S. Novel one-pot synthesis of thiophenols from related triazenes under mild conditions. Synlett, 2012, 23, 1893-1896.
[54]
Zhang, Y.; Li, Y.; Zhang, X.; Jiang, X. Sulfide synthesis through copper-catalyzed C-S bonds formation under biomolecule-compatible conditions. Chem. Commun., 2015, 51, 941-944.
[55]
Li, W.; Beller, M.; Wu, X.F. Catalytic conversion of aryl triazenes into aryl sulfonamides using sulfur dioxide as the sulfonyl source. Chem. Commun., 2014, 50, 9513-9516.
[56]
Wang, C.M.; Sun, H.; Fang, Y.; Huang, Y. General and efficient synthesis of indoles through triazene-directed C-H annulation. Angew. Chem. Int. Ed., 2013, 125, 5907-5910.
[57]
Fang, Y.; Wang, C.G.; Su, S.Q.; Yu, H.Z.; Huang, Y. Selective synthesis of indazoles and indoles via triazene-alkyne cyclization switched by different metals. Org. Biomol. Chem., 2014, 12, 1061-1071.
[58]
Kimball, D.B.; Herges, R.; Haley, M.M. Two unusual, competitive mechanisms for (2-ethynylphenyl)triazene cyclization: Pseudocoarctate versus pericyclic reactivity. J. Am. Chem. Soc., 2002, 124, 1572-1573.
[59]
Kimball, D.B.; Weakley, T.J.R.; Herges, R.; Haley, M.M. Deciphering the mechanistic dichotomy in the cyclization of 1-(2-ethynylphenyl)-3,3-dialkyltriazenes: Competition between pericyclic and pseudocoarctate pathways. J. Am. Chem. Soc., 2002, 124, 13463-13473.
[60]
Kimball, D.B.; Weakley, T.J.R.; Haley, M.M. Cyclization of 1-(2-alkynylphenyl)-3,3-dialkyltriazenes: A convenient, high-yield synthesis of substituted cinnolines and isoindazoles. J. Org. Chem., 2002, 67, 6395-6405.
[61]
Goeminne, A.; Scammells, P.J.; Devine, S.M.; Flynn, B.L. Richter cyclization and co-cyclization reactions of triazene-masked diazonium ions. Tetrahedron Lett., 2010, 51, 6882-6885.
[62]
Yang, W.J.; Yang, Z.J.; Xu, L.J.; Zhang, L.L.; Xu, X.; Miao, M.Z.; Ren, H.J. Surfactant-type brønsted acid catalyzed stereoselective synthesis of trans-3-alkenyl indazoles from triazenylaryl allylic alcohols in water. Angew. Chem. Int. Ed., 2013, 52, 14135-14139.
[63]
Bräse, S.; Dahmen, S.; Heuts, J. Solid-phase synthesis of substituted cinnolines by a richter type cleavage protocol. Tetrahedron Lett., 1999, 40, 6201-6203.
[64]
Vinogradova, O.V.; Sorokoumov, V.N.; Balova, I.A. A short route to 3-alkynyl-4-bromo(chloro)cinnolines by Richter-type cyclization of ortho-(dodeca-1,3-diynyl)aryltriaz-1-enes. Tetrahedron Lett., 2009, 50, 6358-6360.
[65]
Vinogradova, O.V.; Balova, I.A.; Popik, V.V. Synthesis and reactivity of cinnoline-fused cyclic enediyne. J. Org. Chem., 2011, 76, 6937-6941.
[66]
Zhu, C.; Yamane, M. Synthesis of 3,4-disubstituted cinnolines by the Pd-catalyzed annulation of 2-iodophenyltriazenes with an internal alkyne. Tetrahedron, 2011, 67, 4933-4938.
[67]
Liu, C.Y.; Knochel, P. Preparation of polyfunctional arylmagnesium reagents bearing a triazene moiety. A new carbazole synthesis. Org. Lett., 2005, 7, 2543-2546.
[68]
Yang, W.J.; Zhou, J.; Wang, B.J.; Ren, H.J. Lewis acid-promoted synthesis of unsymmetrical and highly functionalized carbazoles and dibenzofurans from biaryl triazenes: Application for the total synthesis of clausine C, clausine clauraila A. Chem. Eur. J., 2011, 17, 13665-13669.
[69]
Shang, X.B.; Xu, L.J.; Yang, W.J.; Zhou, J.; Miao, M.Z.; Ren, H.J. BF3OEt2-Promoted intramolecular nucleophilic substitution; synthesis of dibenzopyranones and coumarins from biaryltriazenes. Eur. J. Org. Chem., 2013, 2013, 5475-5484.
[70]
Chen, Z.; Yang, W.; Xu, L.; Zhang, L.; Miao, M.; Ren, H. BF3OEt2-Promoted tandem O-Arylation/hydroxylation: Efficient synthesis of 2-hydroxyflavanones from triazenylaryl-substituted diketones. Eur. J. Org. Chem., 2013, 2013, 7411-7420.
[71]
Shang, X.B.; Chen, W.Z.; Yao, Y.M. A simple and efficient synthesis of dibenzothiophene via BF3OEt2-promoted intramolecular annulation. Synlett, 2013, 24, 851-854.
[72]
Zhou, J.; Yang, W.J.; Wang, B.J.; Ren, H.J. Friedel crafts arylation for the formation of Csp2-Csp2 bonds: route to unsymmetrical and functionalized polycyclic aromatic hydrocarbons from aryl triazenes. Angew. Chem. Int. Ed., 2012, 51, 12293-12297.
[73]
Hart, H.; Ok, D. Synthesis of 1,5-diamino-1,5-dihydrobenzo[1,2-d:4,5-d’]bistriazole (DABT) and its use as a 1,4-benzadiyne equivalent. J. Org. Chem., 1986, 51, 979-986.
[74]
Charushin, V.N.; Kotovskaya, S.K.; Romanova, S.A.; Chupakhin, O.N.; Tomilov, Y.V.; Nefedov, O.M. 4,5-Difluoro-1,2-dehydrobenzene: Generation and cycloaddition reactions. Mendeleev Commun., 2005, 15, 45-46.
[75]
Androsov, D.A.; Neckers, D.C. Photochemical study of tris(benzotriazol-1-yl)methane. J. Org. Chem., 2007, 72, 1148-1152.
[76]
Kumar, D.; Mishra, B.B.; Tiwari, V.K. Synthesis of 2-N/S/C-substituted benzothiazoles via intramolecular cyclative cleavage of benzotriazole ring. J. Org. Chem., 2013, 79, 251-266.

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