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Synthesis of Amides and Esters by Palladium(0)‐Catalyzed Carbonylative C(sp 3 )−H Activation
Author(s) -
Čarný Tomáš,
Rocaboy Ronan,
Clemenceau Antonin,
Baudoin Olivier
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202007922
Subject(s) - palladium , chemistry , amide , catalysis , carbonylation , ligand (biochemistry) , medicinal chemistry , carbon atom , combinatorial chemistry , stereochemistry , carbon monoxide , organic chemistry , ring (chemistry) , receptor , biochemistry
The 1,4‐palladium shift strategy allows the functionalization of remote C−H bonds that are difficult to reach directly. Reported here is a domino reaction proceeding by C(sp 3 )−H activation, 1,4‐palladium shift, and amino‐ or alkoxycarbonylation, which generates a variety of amides and esters bearing a quaternary β‐carbon atom. Mechanistic studies showed that the aminocarbonylation of the σ‐alkylpalladium intermediate arising from the palladium shift is fast using PPh 3 as the ligand, and leads to the amide rather than the previously reported indanone product.