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Mild, Redox‐Neutral Formylation of Aryl Chlorides through the Photocatalytic Generation of Chlorine Radicals
Author(s) -
Nielsen Matthew K.,
Shields Benjamin J.,
Liu Junyi,
Williams Michael J.,
Zacuto Michael J.,
Doyle Abigail G.
Publication year - 2017
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.201702079
Subject(s) - formylation , chemistry , aryl , carbonylation , redox , catalysis , carbon monoxide , radical , photoredox catalysis , photocatalysis , photochemistry , nickel , chloride , combinatorial chemistry , inorganic chemistry , organic chemistry , alkyl
We report a redox‐neutral formylation of aryl chlorides that proceeds through selective 2‐functionalization of 1,3‐dioxolane through nickel and photoredox catalysis. This scalable benchtop approach provides a distinct advantage over traditional reductive carbonylation in that no carbon monoxide, pressurized gas, or stoichiometric reductant is employed. The mild conditions give unprecedented scope from abundant and complex aryl chloride starting materials.