期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 56, 期 34, 页码 10200-10203出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201705412
关键词
azo compounds; Grignard reagents; nucleophilic addition; organolithium compounds; water chemistry
资金
- University of Bari [Perna01333214Ricat]
- Interuniversities Consortium C.I.N.M.P.I.S. [COCM8470P0]
In contrast to classic methods carried out under inert atmospheres with dry volatile organic solvents and often low temperatures, the addition of highly polar organometallic compounds to non-activated imines and nitriles proceeds quickly, efficiently, and chemoselectively with a broad range of substrates at room temperature and under air with water as the only reaction medium. Secondary amines and tertiary carbinamines are furnished in yields of up to and over 99%. The significant solvent D/H isotope effect observed for the on-water nucleophilic additions of organolithium compounds to imines suggests that the on-water catalysis arises from proton transfer across the organic-water interface. The strong inter-molecular hydrogen bonds between water molecules may play a key role in disfavoring protonolysis, which occurs extensively in other protic media such as methanol. This work lays the foundation for reshaping many fundamental s-block metal-mediated organic transformations in water.
作者
我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。
推荐
暂无数据