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Catalytic vinylogous cross-coupling reactions of rhenium vinylcarbenoids.

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.

SUBMITTER: Chen J

PROVIDER: S-EPMC5909671 | biostudies-literature | 2018 Mar

REPOSITORIES: biostudies-literature

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Catalytic vinylogous cross-coupling reactions of rhenium vinylcarbenoids.

Chen Ji J Wu Jimmy J

Chemical science 20180130 9

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 ...[more]

PMID: 29732125

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