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Reductive Cyclization of Unactivated Alkyl Chlorides with Tethered Alkenes under Visible‐Light Photoredox Catalysis
Author(s) -
Claros Miguel,
Ungeheuer Felix,
Franco Federico,
MartinDiaconescu Vlad,
Casitas Alicia,
LloretFillol Julio
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201812702
Subject(s) - photoredox catalysis , chemistry , alkyl , catalysis , photosensitizer , nucleophile , denticity , photochemistry , cobalt , intramolecular force , visible spectrum , bond cleavage , nickel , combinatorial chemistry , transition metal , metal , photocatalysis , organic chemistry , materials science , optoelectronics
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.