Open AccessNickel-Catalyzed, Stereospecific C–C and C–B Cross-Couplings via C–N and C–O Bond Activation
Author(s) -
Jianyu Xu,
Olivia P. Bercher,
Michael R. Talley,
Mary P. Watson
Publication year - 2021
Publication title -
acs catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 4.898
H-Index - 198
ISSN - 2155-5435
DOI - 10.1021/acscatal.0c05484
Subject(s) - stereocenter , stereospecificity , allylic rearrangement , chemistry , catalysis , reagent , nickel , combinatorial chemistry , functional group , enantioselective synthesis , stereochemistry , organic chemistry , polymer
Highly enantioenriched benzylic and allylic amines and alcohols are readily available via asymmetric synthesis and in complex natural products. The development of mild, nickel-catalyzed cross-couplings of their derivatives has advanced the tools available for the preparation of a range of highly enantioenriched products, including those with quaternary stereocenters. This perspective focuses on cross-couplings with convenient and functional group-tolerant organoboron reagents and highlights the discoveries of activating groups and conditions that have led to high-yielding and highly stereospecific reactions. Emphasis is placed on mechanistic understanding, particularly with regards to controlling inversion vs. retention pathways. Limitations and opportunities for future developments are also highlighted.