[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 BF3•OEt2. 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. BF3•OEt2-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. BF3•OEt2-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 BF3•OEt2-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.