Open AccessSynthesis of Unsaturated Silyl Heterocycles via an Intramolecular Silyl-Heck Reaction
Author(s) -
William B. Reid,
Jesse R. McAtee,
Donald A. Watson
Publication year - 2019
Publication title -
organometallics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.231
H-Index - 172
eISSN - 1520-6041
pISSN - 0276-7333
DOI - 10.1021/acs.organomet.9b00498
Subject(s) - chemistry , intramolecular force , silylation , regioselectivity , heck reaction , alkene , electrophile , palladium , catalysis , medicinal chemistry , organic chemistry
We report the synthesis of unsaturated silacycles via an intramolecular silyl-Heck reaction. Using palladium catalysis, silicon electrophiles tethered to alkenes cyclize to form 5- and 6-membered silicon heterocycles. The effects of alkene substitution and tether length on the efficiency and regioselectivity of the cyclizations are described. Finally, through the use of an intramolecular tether, the first examples of disubstituted alkenes in silyl-Heck reactions are reported.