A highly regio- and stereoselective silylborylation of an alkynylboronate is disclosed. PhMe2Si-Bpin undergoes a Pd(OAc) 2/tOctNC-catalyzed syn-addition to the alkynylboronate to yield 1-phenyl-1-silyl-2,2-diborylethene with high regioselectivity. The product 1-phenyl-1-silyl-2,2-diborylethene is then chemoselectively arylated by Suzuki-Miyaura coupling to afford (Z)-1-silyl-2-borylstilbene derivatives. This approach is extended to the synthesis of a tetraarylated olefin with four different substituents.
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry