Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo 060-0810, Japan.
Org Lett. 2011 Feb 4;13(3):482-5. doi: 10.1021/ol102819k. Epub 2010 Dec 20.
Conjugate addition of alkylboron compounds (alkyl-9-BBN) to imidazol-2-yl α,β-unsaturated ketones proceeded in the presence of a catalytic amount (10 mol %) of CuCl, 1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene (IMes), and t-BuOK. The alkylboranes are available through alkene hydroboration, and thus the overall process represents a reductive conjugate addition of alkenes to enone derivatives. A variety of functional groups are tolerated in both the alkenes and the α,β-unsaturated ketones. The 2-acylimidazole moiety can easily be converted into the corresponding carboxylic acid, ester, and amide derivatives.
烷基硼化合物（烷基-9-BBN）与咪唑-2-基α，β-不饱和酮的共轭加成在催化量（10 mol %）的 CuCl、1,3-双（2,4,6-三甲基苯基）咪唑-2-亚基（IMes）和 t-BuOK 的存在下进行。烷基硼烷可通过烯烃硼氢化得到，因此整个过程代表了烯烃向烯酮衍生物的还原共轭加成。烯烃和α，β-不饱和酮中的各种官能团都可以被容忍。2-酰基咪唑部分可以很容易地转化为相应的羧酸、酯和酰胺衍生物。
