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Highly Regioselective Indoline Synthesis under Nickel/Photoredox Dual Catalysis.

ABSTRACT: Nickel/photoredox catalysis is used to synthesize indolines in one step from iodoacetanilides and alkenes. Very high regioselectivity for 3-substituted indoline products is obtained for both aliphatic and styrenyl olefins. Mechanistic investigations indicate that oxidation to Ni(III) is necessary to perform the difficult C-N bond-forming reductive elimination, producing a Ni(I) complex, which in turn is reduced to Ni(0). This process serves to further demonstrate the utility of photoredox catalysts as controlled single electron transfer agents in multioxidation state nickel catalysis.

SUBMITTER: Tasker SZ

PROVIDER: S-EPMC4586280 | biostudies-literature | 2015 Aug

REPOSITORIES: biostudies-literature

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Highly Regioselective Indoline Synthesis under Nickel/Photoredox Dual Catalysis.

Tasker Sarah Z SZ Jamison Timothy F TF

Journal of the American Chemical Society 20150721 30

Nickel/photoredox catalysis is used to synthesize indolines in one step from iodoacetanilides and alkenes. Very high regioselectivity for 3-substituted indoline products is obtained for both aliphatic and styrenyl olefins. Mechanistic investigations indicate that oxidation to Ni(III) is necessary to perform the difficult C-N bond-forming reductive elimination, producing a Ni(I) complex, which in turn is reduced to Ni(0). This process serves to further demonstrate the utility of photoredox cataly ...[more]

PMID: 26196355

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