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Site-Fixed Hydroboration of Terminal and Internal Alkenes using BX3 /i Pr2 NEt*
Sida Li1,2, Chenyang Hu3, Xin Cui1
1State Key Laboratory for Oxo Synthesis and Selective Oxidation, Suzhou Research Institute of LICP, Lanzhou Institute of Chemical Physics (LICP), Chinese Academy of Sciences, Lanzhou, 730000, China.
Abstract:
An unprecedented and general hydroboration of alkenes with BX3 (X=Br, Cl) as the boration reagent in the presence of i Pr2 NEt is reported. The addition of i Pr2 NEt not only suppresses alkene polymerization and haloboration side reactions but also provides an "H" source for hydroboration. More importantly, the site-fixed installation of a boryl group at the original position of the internal double bond is readily achieved in contrast to conventional transition-metal-catalyzed hydroboration processes. Further application to the synthesis of 1,n-diborylalkanes (n=3-10) is also demonstrated. Preliminary mechanistic studies reveal a major reaction pathway that involves radical species and operates through a frustrated Lewis pair type single-electron-transfer mechanism.
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