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Ascorbic Acid as an Initiator for the Direct C-H Arylation of (Hetero)arenes with Anilines Nitrosated In Situ

AuthorsPinacho Crisóstomo, Fernando R. ; Martín, Tomás ; Carrillo Fumero, Romen
KeywordsMetal‐free reactions
Ascorbic acid
Aromatic substitution
C-H arylation
Green chemistry
Issue Date17-Feb-2014
CitationAngewandte Chemie - International Edition 53(8): 2181-2185 (2014)
AbstractAscorbic 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.
Publisher version (URL)https://doi.org/10.1002/anie.201309761
Identifiersdoi: 10.1002/anie.201309761
issn: 1433-7851
e-issn: 1521-3773
Appears in Collections:(IPNA) Artículos
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