通过氮杂环卡宾活化TMSCN实现羰基化合物的简便氰基硅基化反应。
Activation of TMSCN by N-heterocyclic carbenes for facile cyanosilylation of carbonyl compounds.
作者信息
Song Jinhua J, Gallou Fabrice, Reeves Jonathan T, Tan Zhulin, Yee Nathan K, Senanayake Chris H
机构信息
Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., 900 Old Ridgebury Road, P.O. Box 368, Ridgefield, CT 06877-0368, USA.
出版信息
J Org Chem. 2006 Feb 3;71(3):1273-6. doi: 10.1021/jo052206u.
N-Heterocyclic carbenes were found to be highly effective organocatalysts in activating TMSCN for facile cyanosilylation of carbonyl compounds. Cyano transfer from TMSCN to aldehydes and ketones proceeds at room temperature in the presence of only 0.01-0.5 mol % of N-heterocyclic carbene (1), leading to a range of trimethylsilylated cyanohydrins in very good to excellent yields. These conditions are extremely mild and simple and tolerate various functional groups.
人们发现，N-杂环卡宾是一类高效的有机催化剂，能够活化TMSCN，从而实现羰基化合物的简便氰基硅烷化反应。在仅含0.01 - 0.5 mol% N-杂环卡宾（1）的情况下，TMSCN向醛和酮的氰基转移反应在室温下即可进行，能够以非常好至优异的产率得到一系列三甲基硅基化氰醇。这些反应条件极为温和且简单，并且能够耐受各种官能团。
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