Palladium-catalyzed cross-coupling of stereospecific potassium cyclopropyl trifluoroborates with aryl bromides.
[reaction: see text] Stereospecific cyclopropanation of alkenylboronic esters of pinacol followed by in situ treatment with excess KHF(2) afforded the corresponding potassium cyclopropyl trifluoroborates in high yields, which then underwent Suzuki-Miyaura cross-coupling reactions with aryl bromides to give cyclopropyl-substituted arenes in good yields with retention of configuration. This promises to be a useful method for the synthesis of enantiomerically pure cyclopropanes.
Fang
Guo-Hua
GH
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, PR China.
Yan
Zheng-Jun
ZJ
Deng
Min-Zhi
MZ