期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 140, 期 39, 页码 12415-12423出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.8b05143
关键词
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资金
- NIH/NIGMS [GM087605]
- National Science Foundation [CHE-1464744, CHE1464778, CHE1764298]
- NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [R01GM087605] Funding Source: NIH RePORTER
A method to directly arylate toluene derivatives with aryl bromides to generate diarylmethanes, which are important building blocks in drug discovery, is described. In this method, KN(SiMe3)(2) in combination with a (NIXANTPHOS)Pd catalyst accomplished the deprotonative activation of toluene derivatives to permit cross-coupling with aryl bromides. Good to excellent yields are obtained with a range of electron-rich to neutral aryl bromides. Both electron-rich and electron-poor toluene derivatives are well tolerated, and even 2-chlorotoluene performs well, providing a platform for introduction of additional functionalization. This discovery hinges on the use of a main group metal to activate toluene for deprotonation by means of a cation-pi interaction, which is secured by a bimetallic K-(NDCANTPHOS)Pd assembly. Mechanistic and computational studies support acidification of toluene derivatives by the K+-cation- pi interaction, which may prove pertinent in the development of other, new reaction systems.
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