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Murahashi Cross‐Coupling at −78 °C: A One‐Pot Procedure for Sequential C−C/C−C, C−C/C−N, and C−C/C−S Cross‐Coupling of Bromo‐Chloro‐Arenes
Author(s) -
Sinha Narayan,
Heijnen Dorus,
Feringa Ben L.,
Organ Michael G.
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201901678
Subject(s) - c band , hla c , c met , chemistry , coupling (piping) , materials science , physics , optics , metallurgy , biochemistry , allele , receptor , gene , hepatocyte growth factor
The coupling of organolithium reagents, including strongly hindered examples, at cryogenic temperatures (as low as −78 °C) has been achieved with high‐reactivity Pd‐NHC catalysts. A temperature‐dependent chemoselectivity trigger has been developed for the selective coupling of aryl bromides in the presence of chlorides. Building on this, a one‐pot, sequential coupling strategy is presented for the rapid construction of advanced building blocks. Importantly, one‐shot addition of alkyllithium compounds to Pd cross‐coupling reactions has been achieved, eliminating the need for slow addition by syringe pump.