Tetrahedron Letters

Organic synthesis using haloboration reaction. I. A simple and selective synthesis of 2-bromo-and 2-iodo-1-alkenes

S Hara, H Dojo, S Takinami, A Suzuki

Index: Hara, Shoji; Dojo, Hidetaka; Takinami, Satoru; Suzuki, Akira Tetrahedron Letters, 1983 , vol. 24, # 7 p. 731 - 734

Full Text: HTML

Citation Number: 134

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 XB moiety to C C bonds and cis fashion. The bromoboration reaction occurs chemoselectively at terminal C C bonds but not at internal C C, terminal and internal C C bonds. The protonolysis of haloboration products with acetic acid gives corresponding 2-bromo-or 2- ...