硅胶通过 N-杂环卡宾硼烷促进醛酮的还原。

Silica gel promotes reductions of aldehydes and ketones by N-heterocyclic carbene boranes.

机构信息

Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA.

出版信息

Org Lett. 2012 Sep 7;14(17):4540-3. doi: 10.1021/ol302010f. Epub 2012 Aug 16.

DOI:10.1021/ol302010f

Abstract

N-Heterocyclic carbene boranes (NHC-boranes) such as 1,3-dimethylimidazol-2-ylidine trihydridoborane (diMe-Imd-BH(3)) serve as practical hydride donors for the reduction of aldehydes and ketones in the presence of silica gel. Primary and secondary alcohols are formed in good yields under ambient conditions. Aldehydes are selectively reduced in the presence of ketones. One, two, or even all three of the boron hydrides can be transferred. The process is attractive because all the components are stable and easy to handle and because both the reaction and isolation procedures are convenient.

摘要

N-杂环卡宾硼烷（NHC-硼烷），如 1,3-二甲基咪唑-2-亚基三氢硼烷（二甲基-Imd-BH(3)），在硅胶存在下作为还原醛和酮的实用氢供体。在环境条件下，伯醇和仲醇以良好的收率生成。在酮存在下，醛被选择性还原。一个、两个甚至三个硼氢化物都可以转移。该过程具有吸引力，因为所有的成分都稳定且易于处理，并且反应和分离过程都很方便。