Shoji Hara, Hidetaka Dojo, Satoru Takinami
1983
Citations
0
Influential Citations
93
Citations
Quality indicators
Journal
Tetrahedron Letters
Abstract
Abstract B-bromo- or B-iodo-9-borabicyclo[3.3.1]nonane reacts readily with 1-alkynes. Such haloboration reactions proceed through the Markovnikov addition of the X-B moiety to CC bonds and cis fashion. The bromoboration reaction occurs chemoselectively at terminal CC bonds but not at internal CC, terminal and internal CC bonds. The protonolysis of haloboration products with acetic acid gives corresponding 2-bromo- or 2-iodo-1-alkenes in excellent yields.