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. 2022 May 30;13(24):7256-7263.
doi: 10.1039/d2sc02277j. eCollection 2022 Jun 22.

Three-component carboacylation of alkenes via cooperative nickelaphotoredox catalysis

Dingyi Wang  1 , Lutz Ackermann  1   2
Affiliations

Three-component carboacylation of alkenes via cooperative nickelaphotoredox catalysis

Dingyi Wang et al. Chem Sci. .

Abstract

Various commercially available acyl chlorides, aldehydes, and alkanes were exploited for versatile three-component 1,2-carboacylations of alkenes to forge two vicinal C-C bonds through the cooperative action of nickel and sodium decatungstate catalysis. A wealth of ketones with high levels of structural complexity was rapidly obtained via direct functionalization of C(sp2)/C(sp3)-H bonds in a modular manner. Furthermore, a regioselective late-stage modification of natural products showcased the practical utility of the strategy, generally featuring high resource economy and ample substrate scope.

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Conflict of interest statement

There are no conflicts to declare.

Figures

Scheme 1
Scheme 1. Synthetic approaches to carbonyl compounds.
Scheme 2
Scheme 2. Synthetic applications.
Scheme 3
Scheme 3. Late-stage functionalization of complex molecules. a Reaction conditions: 1 (1 mmol), 2 (0.4 mmol), 3 (0.2 mmol), Ni(dtbbpy)Br2 (10 mol%), NaDT (2 mol%), K2HPO4 (0.4 mmol) in acetone (0.2 M) at 30 °C under irradiation of LEDs (10 W, λ = 390 nm) for 24 hours. b1 (0.2 mmol), 2 (0.6 mmol), 3 (0.6 mmol), Ni(dtbbpy)Br2 (10 mol%), NaDT (2 mol%), K2HPO4 (0.4 mmol) in acetone (0.2 M) at 30 °C under irradiation of LEDs (10 W, λ = 390 nm) for 24 hours.
Scheme 4
Scheme 4. Mechanistic experiments.
Scheme 5
Scheme 5. Proposed mechanism.
See this image and copyright information in PMC

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