Nishimoto Y, Takeuchi M, Yasuda M, Baba A * Osaka University, Japan
Synthesis of Alkylbismuths by Regiodivergent Carbobismuthination of Simple Alkenes.
Chem. Eur. J. 2013;
19: 14411-14415
Significance
Baba and co-workers report a novel carbobismuthination reaction of alkenes using bismuth
trihalides and ketene silyl acetals. Furthermore, in this protocol, the first switch
in regioselectivity of the carbometalation using BiCl3 instead of BiBr3 is reported.
Comment
The resultant alkylbismuth compounds react with a range of reagents in order to give
functionalized aliphatics. Therefore, reaction with N-bromosuccinimide furnishes the bromide, reaction with AIBN and PhSSPh introduces
a thiophenyl group, and PhI(OAc)2 in combination with TMSOAc gives the acetate.
