A dancing nickel in asymmetric catalysis: Enantioselective synthesis of boronic esters by 1,1-addition to terminal alkenes
Year: 2020
Type: article
Abstract: Chiral benzylic boronic esters were synthesized through a simple three-component reaction involving a terminal alkene, an aryl bromide and B2pin2 using a nickel catalyst. Interestingly, the reaction yielded a 1,1-difunctionalized alkane instead of a 1,2-difunctionalized product. Mechanistic investigations supported a 1,2-Ni migration to achieve the 1,1-difunctionalized product. The 1,1-addition addition products were obtained in good yields and high chemo and regio-selectivity without the need for directing groups. When a chiral Ni catalyst was employed, the resulting boronic esters were prepared with excellent enantioselectivity.
Source: Green Synthesis and Catalysis
Authors: Bethany J. McCarty, Weiping Tang
Institution: University of Wisconsin–Madison
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: diamond
OpenAlex ID: W3114870508