期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 53, 期 23, 页码 5969-5973出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201400889
关键词
addition reactions; deep eutectic solvents; green chemistry; Grignard reagents; organolithium compounds
资金
- MICINN of Spain [CTQ2010-14796, RYC-2011-08451]
- MICINN
- European ERCSocial Fund
- Royal Society
- European Research Council (ERC)
Despite their enormous synthetic relevance, the use of polar organolithium and Grignard reagents is greatly limited by their requirements of low temperatures in order to control their reactivity as well as the need of dry organic solvents and inert atmosphere protocols to avoid their fast decomposition. Breaking new ground on the applications of these commodity organometallics in synthesis under more environmentally friendly conditions, this work introduces deep eutetic solvents (DESs) as a green alternative media to carry out chemoselective additions of ketones in air at room temperature. Comparing their reactivities in DES with those observed in pure water suggest that a kinetic activation of the alkylating reagents is taking place, favoring nucleophilic addition over the competitive hydrolysis, which can be rationalized through formation of halide-rich magnesiate or lithiate species.
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