Regio- and Stereoselective Carbobismuthination of Alkynes


  • This work was supported by a Grant-in-Aid for Scientific Research on Innovative Areas (No. 22106527, “Organic Synthesis Based on Reaction Integration. Development of New Methods and Creation of New Substances” and No. 23105525, “Molecular Activation Directed toward Straightforward Synthesis”) and Challenging Exploratory Research (No. 23655083) from the Ministry of Education, Culture, Sports, Science and Technology (Japan). We thank Dr. Nobuko Kanehisa for valuable advice regarding X-ray crystallography.


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Three become one: The first carbobismuthination of alkynes has been accomplished by the simple reaction of an alkyne, BiBr3, and a ketene silyl acetal to produce an alkenylbismuth with high stereo- and regioselectivity (see scheme). X-ray crystallographic analysis of the alkenylbismuth product and control experiments using α-bismuthino ester revealed the reaction mechanism.