Premium
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
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201812702
Subject(s) - chemistry , photoredox catalysis , alkyl , photochemistry , catalysis , nucleophile , photosensitizer , denticity , intramolecular force , alkene , cobalt , visible spectrum , bond cleavage , combinatorial chemistry , photocatalysis , metal , organic chemistry , physics , 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.