Aqueous Sodium Hydroxide Promoted Cross-Coupling Reactions of Alkenyltrialkoxysilanes under Ligand-Free Conditions
作者:Emilio Alacid、Carmen Nájera
DOI:10.1021/jo702570q
日期:2008.3.1
alkenyltrialkoxysilanes with aryl iodides, bromides, and chlorides are performed on water using sodium hydroxide as activator at 120 °C under normal or microwave heating. This process occurs in the presence of Pd(OAc)2 or 4-hydroxyacetophenone oxime-derived palladacycle 1 as precatalysts under ligand-free conditions with low Pd loadings (0.01−1 mol %) and using tetra-n-butylammonium bromide as additive. Different
copper(I) oxide are reported. The process is catalyzed by HCl which can be in situ generated via hydrolysis of chlorosilanes by traces of water present in the system. An appearance of olefin/CuCl π‐intermediates can provide a stereoselectivity of the process and alter the pathway of siloxanes formation employing Cu2O as the source of oxygen. It was also shown that acetonitrile may be available as a solvent
Zhun', V. I.; Zhun', A. B.; Vlasenko, S. D., Journal of general chemistry of the USSR, 1982, vol. 52, # 11, p. 2266 - 2270
作者:Zhun', V. I.、Zhun', A. B.、Vlasenko, S. D.、Belorusskaya, L. A.、Chernyshev, E. A.、Sheludyakov, V. D.
DOI:——
日期:——
Cross-coupling of vinylpolysiloxanes with aryl iodides
作者:Scott E. Denmark、Zhigang Wang
DOI:10.1016/s0022-328x(00)00894-9
日期:2001.4
Commercially available vinylpolysiloxane (1) rapidly undergoes cross-coupling reactions with aryl and alkenyl iodides in the presence of tetrabutylammonium fluoride (two to three equivalents) and Pd(dba)(2) (1-5 mol%) at room temperature to afford coupling products in high yield. This process employs an inexpensive and non-toxic siloxane reagent and shows good functional group compatibility and high stereospecificity. (C) 2001 Elsevier Science B.V. All rights reserved.
Cherepennikova, N. F.; Semenov, V. V., Journal of general chemistry of the USSR, 1989, vol. 59, # 4, p. 848