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Direct β‐ and γ‐C(sp 3 )−H Alkynylation of Free Carboxylic Acids **
Author(s) -
Ghiringhelli Francesca,
Uttry Alexander,
Ghosh Kiron Kumar,
Gemmeren Manuel
Publication year - 2020
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.202010784
Subject(s) - alkynylation , carboxylic acid , enantioselective synthesis , chemistry , combinatorial chemistry , palladium , catalysis , stereochemistry , organic chemistry
In this study we report the identification of a novel class of ligands for palladium‐catalyzed C(sp 3 )−H activation that enables the direct alkynylation of free carboxylic acid substrates. In contrast to previous synthetic methods, no introduction/removal of an exogenous directing group is required. A broad scope of acids including both α‐quaternary and challenging α‐non‐quaternary can be used as substrates. Additionally, the alkynylation in the distal γ‐position is reported. Finally, this study encompasses preliminary findings on an enantioselective variant of the title transformation as well as synthetic applications of the products obtained.