Rhodium-katalysierte Addition von Diphenylacetylen an Azobenzol: ein neuer Weg zu Indolderivaten
作者： P. Rei�er , Y. Wakatsuki , H. Kisch
DOI: 10.1007/BF00811752
关键词: Chemistry 、 Diphenylacetylene 、 Azobenzene 、 Medicinal chemistry
摘要: RhCl(PPh3)3 katalysiert die Bildung von N-Anilino-2,3-diphenylindol (1) und kleiner Mengen 2,3-Diphenylindol (2) aus Azobenzol Diphenylacetylen. Schwache Sauren Kieselgel beschleunigen Reaktion furhren zu einer nahezu quantitativen von1. Andere Rhodium(I)-Komplexe sind weniger aktiv Rh(III)-Verbindungen wirken inhibierend. Die Strukturen zweier Schlusselintermediate des postulierten Katalysezyklus werden durchab initio MO-Rechnungen bestatigt..
springer.com
sci-hub.se 参考文章(27)
R.J. Sundberg, 3.06 – Pyrroles and their Benzo Derivatives: (iii) Synthesis and Applications Reference Module in Chemistry, Molecular Sciences and Chemical Engineering#R##N#Comprehensive Heterocyclic Chemistry. ,vol. 3, pp. 313- 376 ,(1984) , 10.1016/B978-008096519-2.00056-4
Ronald S. Dickson, Homogeneous Catalysis with Compounds of Rhodium and Iridium ,(1985)
M.I. Bruce, M.Z. Iqbal, F.G.A. Stone, Ortho-Metallation reactions Journal of Organometallic Chemistry. ,vol. 40, pp. 393- 401 ,(1972) , 10.1016/S0022-328X(00)93379-5
M. I. Bruce, B. L. Goodall, The transition metal chemistry of azo compounds John Wiley & Sons, Ltd.. pp. 259- 311 ,(2004) , 10.1002/0470023414.CH9
M Baudler, Georg Brauer, Handbuch der präparativen anorganischen Chemie Published in <b>1975</b> in Stuttgart by Enke. ,(1954)
C. Daniel, N. Koga, J. Han, X. Y. Fu, K. Morokuma, Ab initio MO study of the full catalytic cycle of olefin hydrogenation by the Wilkinson catalyst RhCl(PR3)3 Journal of the American Chemical Society. ,vol. 110, pp. 3773- 3787 ,(1988) , 10.1021/JA00220A010
Yoshihisa Watanabe, Michihiro Yamamoto, Sang Chul Shim, Sogo Miyanaga, Take-aki Mitsudo, The transition metal-catalyzed N-heterocyclization. The rhodium-catalyzed synthesis of indoles. Chemistry Letters. ,vol. 9, pp. 603- 604 ,(1980) , 10.1246/CL.1980.603
Richard C. Larock, Eul Kgun Yum, Synthesis of indoles via palladium-catalyzed heteroannulation of internal alkynes Journal of the American Chemical Society. ,vol. 113, pp. 6689- 6690 ,(1991) , 10.1021/JA00017A059
W. J. Hehre, R. F. Stewart, J. A. Pople, Self‐Consistent Molecular‐Orbital Methods. I. Use of Gaussian Expansions of Slater‐Type Atomic Orbitals The Journal of Chemical Physics. ,vol. 51, pp. 2657- 2664 ,(1969) , 10.1063/1.1672392
Sei Otsuka, T. Yoshida, Y. Tatsuno, Isocyanide-nickel(0) and -palladium(0) complexes involving unsaturated ligands Journal of the American Chemical Society. ,vol. 93, pp. 6462- 6469 ,(1971) , 10.1021/JA00753A021