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Ascorbic Acid as an Initiator for the Direct CH Arylation of (Hetero)arenes with Anilines Nitrosated In Situ
Author(s) -
Crisóstomo Fernando Pinacho,
Martín Tomás,
Carrillo Romen
Publication year - 2014
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.201309761
Subject(s) - homolysis , chemistry , ascorbic acid , aniline , aryl , radical initiator , in situ , polymer chemistry , vitamin c , radical , medicinal chemistry , organic chemistry , photochemistry , combinatorial chemistry , monomer , polymer , alkyl , food science
Ascorbic acid (vitamin C) has been used as a radical initiator in a metal‐free direct CH arylation of (hetero)arenes. Starting from an aniline, the corresponding arenediazonium ion is generated in situ and immediately reduced by vitamin C to an aryl radical that undergoes a homolytic aromatic substitution with a (hetero)arene. Notably, neither heating nor irradiation is required. This procedure is mild, operationally simple, and constitutes a greener approach to arylation.