A dancing nickel in asymmetric catalysis: Enantioselective synthesis of boronic esters by 1,1-addition to terminal alkenes

Green Synthesis and Catalysis

Weiping Tang¹  Bethany J. McCarty² 

[1] Department of Chemistry, University of Wisconsin-Madison, Madison, WI 53706, United States;School of Pharmacy, University of Wisconsin-Madison, Madison, WI 53705, United States;

关键词: Nickel;    Asymmetric;    Catalysis;    Boronic esters;    1,1-Addition;    Terminal alkenes;   

DOI  :  

来源: DOAJ

【 摘 要 】

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.

【 授权许可】

Unknown