4.8 Article

Photochemical Asymmetric Nickel-Catalyzed Acyl Cross-Coupling

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 47, Pages 16854-16858

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201910168

Keywords

asymmetric catalysis; cross-coupling; nickel catalysis; photochemistry; radical chemistry

Funding

  1. MICIU [CTQ2016-75520P]
  2. AGAUR [2017 SGR 981]
  3. European Research Council [ERC-2015-CoG 681840 - CATA-LUX]

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Photochemical enantioselective nickel-catalyzed cross-coupling reactions are difficult to implement. We report a visible-light-mediated strategy that successfully couples symmetrical anhydrides and 4-alkyl dihydropyridines (DHPs) to afford enantioenriched alpha-substituted ketones under mild conditions. The chemistry does not require exogenous photocatalysts. It is triggered by the direct excitation of DHPs, which act as a radical source and as a reductant, facilitating the turnover of the chiral catalytic nickel complex.

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