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Merging Electron Transfer with 1,2‐Metalate Rearrangement: Deoxygenative Arylation of Aromatic Amides with Arylboronic Esters
Author(s) -
Jiao Jiwen,
Wang Xiaoming
Publication year - 2021
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.202104359
Subject(s) - chemistry , amide , reagent , combinatorial chemistry , peptide bond , electron transfer , organic chemistry , enzyme
Amides are essentially inert carboxyl derivatives in many types of chemical transformations. In particular, deoxygenative C−C bond formation of amides to synthetically important amines is a long‐standing challenge for synthetic chemists due to the inertness of the resonance‐stabilized amide C=O bond. Herein, it is disclosed that by merging electron‐transfer‐induced activation with 1,2‐metalate rearrangement, a wide range of aromatic amides react smoothly with arylboron reagents, affording a series of biologically relevant diarylmethylamines as deoxygenative C−C bond cross‐coupling products. With its simplicity and versatility, this reaction shows great promise in the synthesis of amines from amides, which may open up new avenues in retrosynthetic planning and find widespread use in academia and industry.