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Photo‐Organocatalysis of Atom‐Transfer Radical Additions to Alkenes
Author(s) -
Arceo Elena,
Montroni Elisa,
Melchiorre Paolo
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201406450
Subject(s) - chemistry , organocatalysis , photochemistry , intermolecular force , catalysis , atom transfer radical polymerization , organic synthesis , radical , halide , reactive intermediate , photoredox catalysis , molecule , organic chemistry , enantioselective synthesis , polymer , photocatalysis , polymerization
We have found that an organic molecule as simple as p ‐anisaldehyde efficiently catalyzes the intermolecular atom‐transfer radical addition (ATRA) of a variety of haloalkanes onto olefins, one of the fundamental carbon–carbon bond‐forming transformations in organic chemistry. The reaction requires exceptionally mild reaction conditions to proceed, as it occurs at ambient temperature and under illumination by a readily available fluorescent light bulb. Initial investigations support a mechanism whereby the aldehydic catalyst photochemically generates the reactive radical species by sensitization of the organic halides by an energy‐transfer pathway.