作者:David J. Zillman、Gloria C. Hincapié、M. Reza Savari、Farhad G. Mizori、Thomas E. Cole
DOI:10.1016/j.tetlet.2010.03.096
日期:2010.6
Mixed organoboranes based on diphenyl- or dimethylalkylboranes transfer the alkyl group in the reductive alkylation of p-benzoquinone to form the alkylhydroquinones in very high yields. The auxiliary groups do not transfer or have a low migratory aptitude. Primary and secondary alkyl groups are transferred with retention of regio- and stereochemistry to the hydroquinone. O-Alkylation is the major product
基于二苯基或dimethylalkylboranes混合在有机硼烷的还原性烷基化转移烷基p苯醌以形成非常高的产率的alkylhydroquinones。辅助团体不会转移或具有较低的迁徙能力。伯烷基和仲烷基在保留区域和立体化学的情况下转移至氢醌。O-烷基化是主要的产物,其具有在附接部位附近具有立体体积的叔和仲基团。金属盐例如镁的存在导致还原为未取代的氢醌。该反应是通过有机硼烷制得烷基氢醌的第一个实用途径。