期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 58, 期 15, 页码 4869-4874出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201812702
关键词
cyclizations; haloalkanes; photochemistry; reaction mechanisms; synthetic methods
资金
- ICIQ Foundation
- Cellex Foundation
- European Research Council [ERC-CG-2014-648304]
- MINECO [CTQ2016-80038-R]
- Juan de la Cierva-Incorporacion contract
The chemical inertness of abundant and commercially available alkyl chlorides precludes their widespread use as reactants in chemical transformations. Presented in this work is a metallaphotoredox methodology to achieve the catalytic intramolecular reductive cyclization of unactivated alkyl chlorides with tethered alkenes. The cleavage of strong C(sp(3))-Cl bonds is mediated by a highly nucleophilic low-valent cobalt or nickel intermediate generated by visible-light photoredox reduction employing a copper photosensitizer. The high basicity and multidentate nature of the ligands are key to obtaining efficient metal catalysts for the functionalization of unactivated alkyl chlorides.
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