期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 59, 期 47, 页码 21121-21128出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202008630
关键词
alkenes; amino acids; carbon dioxide; photocatalysis; reaction mechanisms
资金
- National Natural Science Foundation of China [21822108, 21822303, 21772129, 21772020]
- Fok Ying Tung Education Foundation [161013]
- Sichuan Science and Technology Program [20CXTD0112]
- Fundamental Research Funds for the Central Universities
Remote difunctionalization of unactivated alkenes is challenging but a highly attractive tactic to install two functional groups across long distances. Reported herein is the first remote difunctionalization of alkenes with CO2. This visible-light photoredox catalysis strategy provides a facile method to synthesize a series of carboxylic acids bearing valuable fluorine- or phosphorus-containing functional groups. Moreover, this versatile protocol shows mild reaction conditions, broad substrate scope, and good functional-group tolerance. Based on DFT calculations, a radical adds to an unactivated alkene to smoothly form a new carbon radical, followed by a 1,5-hydrogen atom-transfer process, the rate-limiting step, generating a more stable benzylic radical. The reduction of the benzylic radicals by an Ir(II)species generates the corresponding benzylic carbanions as the key intermediates, which further undergo nucleophilic attack with CO(2)to generate carboxylates.
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