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Palladium‐Catalyzed C−H Alkynylation of Unactivated Alkenes
Author(s) -
Schreib Benedikt S.,
Fadel Marlene,
Carreira Erick M.
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.202000935
Subject(s) - palladium , olefin fiber , catalysis , stereospecificity , yield (engineering) , alkynylation , chemistry , surface modification , combinatorial chemistry , medicinal chemistry , organic chemistry , materials science , metallurgy
Abstract Palladium‐catalyzed regio‐ and diastereoselective C−H functionalization with bromoalkynes and electronically unbiased olefins is reported. The picolinamide directing group enables the formation of putative 5 and 6‐exo‐metallacycles as intermediates to afford monoalkynylated products in up to 91 % yield in a stereospecific fashion. The systematic study reveals that substrates with a wide range of substituents on the olefin and bromoalkyne coupling partners are tolerated. Chemoselective transformations were demonstrated for the obtained amides, olefins, and alkynes.