anti-Carbobismuthination of Alkynes

Paul Knochel; Andreas K. Steib

doi:10.1055/s-0031-1290538

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Synfacts 2012; 8(4): 0427
DOI: 10.1055/s-0031-1290538

Metal-Mediated Synthesis

anti-Carbobismuthination of Alkynes

Contributor(s):

Paul Knochel

,

Andreas K. Steib

Nishimoto Y, Takeuchi M, Yasuda M, Baba A * Osaka University, Suita, Japan
Regio- and Stereoselective Carbobismuthination of Alkynes.

Angew. Chem. Int. Ed. 2012;
51: 1051-1054

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Publication History

Publication Date:
20 March 2012 (online)

Abstract
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Key words

bismuth - alkynes - carbobismuth-ination

Significance

The first carbobismuthination of alkynes has been accomplished by the reaction of an alkyne, BiBr₃, and a ketene silyl acetal to produce an alkenylbismuth compound with high stereo- and regioselectivity. The Br₂Bi group in the alkenylbismuth compounds can be substituted by I, Ts and SPh groups, and palladium-catalyzed cross-couplings with acid chlorides have been performed successfully.

Comment

The reaction of BiBr₃ with a phenylacetylene derivative and a ketene silyl acetal gives monoalkenylbismuth dibromide as a white solid. X-ray crystallographic analysis of this product reveals that the carbobismuthination takes place regio- and stereoselectively in an anti-addition manner.

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