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Double Deprotonation of Pyridinols Generates Potent Organic Electron‐Donor Initiators for Haloarene–Arene Coupling
Author(s) -
Barham Joshua P.,
Coulthard Graeme,
Kane Ryan G.,
Delgado Nathan,
John Matthew P.,
Murphy John A.
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201511847
Subject(s) - chemistry , deprotonation , aryl , organic synthesis , alkali metal , coupling reaction , photochemistry , combinatorial chemistry , organic chemistry , polymer chemistry , catalysis , ion , alkyl
Transition metal‐free couplings of haloarenes with arenes, triggered by the use of alkali metal alkoxides in the presence of an organic additive, are receiving significant attention in the literature. Most of the known organic additives effect coupling of iodoarenes, but not bromoarenes, to arenes. Recently it was reported that 2‐pyridinecarbinol ( 11 ) extends the reaction to aryl bromides. This paper investigates the mechanism, and reports evidence for dianions derived from 11 as electron donors to initiate the reaction. It also proposes routes by which electron‐poor benzoyl derivatives can be transformed into electron donors to initiate these reactions.