Sarah M Pound1, Mary P Watson. 1. Department of Chemistry & Biochemistry, University of Delaware, Newark, Delaware 19716, USA. mpwatson@udel.edu.
Abstract
This perspective showcases our development of benzylic and allylic amine and alcohol derivatives as electrophiles for stereospecific, nickel-catalyzed cross-coupling reactions, as well as the prior art that inspired our efforts. The success of our effort has relied on the use of benzyl ammonium triflates as electrophiles for cross-couplings via C-N bond activation and benzylic and allylic carboxylates for cross-couplings via C-O bond activation. Our work, along with others' exciting discoveries, has demonstrated the potential of stereospecific, nickel-catalyzed cross-couplings of alkyl electrophiles in asymmetric synthesis, and enables efficient generation of both tertiary and quaternary stereocenters.
This perspective showcases our development of benzylic and n class="Chemical">allylic amine and alcohol derivatives as electrophiles for stereospecific, nickel-catalyzed cross-coupling reactions, as well as the prior art that inspired our efforts. The success of our effort has relied on the use of benzyl ammonium triflates as electrophiles for cross-couplings via C-N bond activation and benzylic and allylic carboxylates for cross-couplings via C-O bond activation. Our work, along with others' exciting discoveries, has demonstrated the potential of stereospecific, nickel-catalyzed cross-couplings of alkyl electrophiles in asymmetric synthesis, and enables efficient generation of both tertiary and quaternary stereocenters.
Authors: Sergei Tcyrulnikov; Qiuqi Cai; J Cameron Twitty; Jianyu Xu; Abderrahman Atifi; Olivia P Bercher; Glenn P A Yap; Joel Rosenthal; Mary P Watson; Marisa C Kozlowski Journal: ACS Catal Date: 2021-06-28 Impact factor: 13.700