期刊
CHEMICAL SCIENCE
卷 10, 期 47, 页码 10937-10943出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c9sc03737c
关键词
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资金
- Canada Research Chair Foundation
- CFI
- FRQNT Center for Green Chemistry and Catalysis
- McGill University
- NSERC [RGPIN-2016-05059]
- McGill's Chemistry Department
- CONACYT Mexico [2018-000009-01EXTF-00413]
- NSERC
Efficient carbon-carbon bond formation is of great importance in modern organic synthetic chemistry. The pinacol coupling discovered over a century ago is still one of the most efficient coupling reactions to build the C-C bond in one step. However, traditional pinacol coupling often requires over-stoichiometric amounts of active metals as reductants, causing long-lasting metal waste issues and sustainability concerns. A great scientific challenge is to design a metal-free approach to the pinacol coupling reaction. Herein, we describe a light-driven pinacol coupling protocol without use of any metals, but with N2H4, used as a clean non-metallic hydrogen-atom-transfer (HAT) reductant. In this transformation, only traceless non-toxic N-2 and H-2 gases were produced as by-products with a relatively broad aromatic ketone scope and good functional group tolerance. A combined experimental and computational investigation of the mechanism suggests that this novel pinacol coupling reaction proceeds via a HAT process between photo-excited ketone and N2H4, instead of the common single-electron-transfer (SET) process for metal reductants.
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