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Catalytic 1,4-rhodium(III) migration enables 1,3-enynes to function as one-carbon oxidative annulation partners in C-H functionalizations.

ABSTRACT: 1,3-Enynes containing allylic hydrogens cis to the alkyne are shown to act as one-carbon partners, rather than two-carbon partners, in various rhodium-catalyzed oxidative annulations. The mechanism of these unexpected transformations is proposed to occur through double C-H activation, involving a hitherto rare example of the 1,4-migration of a Rh(III) species. This phenomenon is general across a variety of substrates, and provides a diverse range of heterocyclic products.

SUBMITTER: Burns DJ

PROVIDER: S-EPMC4464529 | biostudies-literature | 2014 Sep

REPOSITORIES: biostudies-literature

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Catalytic 1,4-rhodium(III) migration enables 1,3-enynes to function as one-carbon oxidative annulation partners in C-H functionalizations.

Burns David J DJ Lam Hon Wai HW

Angewandte Chemie (International ed. in English) 20140722 37

1,3-Enynes containing allylic hydrogens cis to the alkyne are shown to act as one-carbon partners, rather than two-carbon partners, in various rhodium-catalyzed oxidative annulations. The mechanism of these unexpected transformations is proposed to occur through double C-H activation, involving a hitherto rare example of the 1,4-migration of a Rh(III) species. This phenomenon is general across a variety of substrates, and provides a diverse range of heterocyclic products. ...[more]

PMID: 25048465

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