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Direct ?-heteroarylation of amides (? to nitrogen) and ethers through a benzaldehyde-mediated photoredox reaction.

ABSTRACT: A photoredox reaction for cross-dehydrogenative coupling (CDC) was developed to C?-arylate amides (? to nitrogen) and ethers using a variety of five- and six-membered electron-deficient heteroarenes. A unique decomposition mechanism of ammonium persulfate enhanced by photoexcited benzaldehydes was revealed. This benzaldehyde-mediated photoredox reaction proceeded smoothly with household 23 W CFL bulbs as the energy source under metal-free conditions, allowing the construction of new Csp2 -Csp2 and Csp3 -Csp2 bonds and access to important pharmacophores of broad utility using commercially available reagents.

SUBMITTER: Zhang Y

PROVIDER: S-EPMC5968545 | biostudies-literature | 2016 Mar

REPOSITORIES: biostudies-literature

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Direct α-heteroarylation of amides (α to nitrogen) and ethers through a benzaldehyde-mediated photoredox reaction.

Zhang Yongqiang Y Teuscher Kevin B KB Ji Haitao H

Chemical science 20151207 3

A photoredox reaction for cross-dehydrogenative coupling (CDC) was developed to Cα-arylate amides (α to nitrogen) and ethers using a variety of five- and six-membered electron-deficient heteroarenes. A unique decomposition mechanism of ammonium persulfate enhanced by photoexcited benzaldehydes was revealed. This benzaldehyde-mediated photoredox reaction proceeded smoothly with household 23 W CFL bulbs as the energy source under metal-free conditions, allowing the construction of new C ...[more]

PMID: 29899938

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