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Synfacts 2014; 10(1): 0080
DOI: 10.1055/s-0033-1340367
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Bismuth-Mediated Switchable Regioselective Carbometalation

Contributor(s):
Paul Knochel
,
Andreas K. Steib
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
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Further Information

Publication History

Publication Date:
13 December 2013 (online)

 
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Key words

bismuth - alkenes

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.


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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.


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