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Updated: Feb 11, 2026

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Catalytic vinylogous cross-coupling reactions of rhenium vinylcarbenoids
1Department of Chemistry , Dartmouth College , Hanover , New Hampshire 03755 , USA .
Abstract:
We report the first example of the rhenium-catalyzed allylation reaction of indolyl compounds by means of cross-coupling with propargyl ethers as non-obvious allylating reagents. Data from isotope-labeling and kinetic isotopic studies are consistent with a mechanism that proceeds by vinylidene formation as the rate determining step, followed by 1,5-hydride shift to generate a key rhenium vinylcarbenoid complex. Bond formation occurs at the vinylogous site and the reaction is conveniently carried out in air.
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