Tetrahedron Letters p. 731 - 734 (1983)
Update date:2022-08-02
Topics:
Hara, Shoji
Dojo, Hidetaka
Takinami, Satoru
Suzuki, Akira
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 C<*>C bonds and cis fashion.The bromoboration reaction occours 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-iodo-1-alkenes in excellent yields.
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