4.8 Article

Photo-Promoted Decarboxylative Alkylation of α,β-Unsaturated Carboxylic Acids with ICH2CN for the Synthesis of β,γ-Unsaturated Nitriles

Journal

ORGANIC LETTERS
Volume 23, Issue 18, Pages 7188-7193

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c02585

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Funding

  1. National Natural Science Foundation of China [21961045, 22061048]
  2. Reserve Talents of Young and Middle-aged Academic Leaders of Yunnan Province [202005AC160016]
  3. Yunnan Provincial Key Laboratory Construction Plan Funding of Universities
  4. Yunnan Provincial Engineering Research Center Construction Plan Funding of Universities

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An efficient, catalyst/photocatalyst-free, and cost-effective methodology has been developed for the synthesis of beta,gamma-unsaturated nitriles from alpha,beta-unsaturated carboxylic acids. The reaction proceeded in an environmentally benign atmosphere of blue light-emitting diode irradiation with K2CO3 and water at room temperature, showing high yields (up to 83%) with a wide range of substrates.
An efficient, catalyst/photocatalyst-free, and cost-effective methodology for the decarboxylative alkylation of alpha,beta-unsaturated carboxylic acids to synthesize beta,gamma-unsaturated nitriles has been developed. The reaction proceeded in an environmentally benign atmosphere of blue light-emitting diode irradiation with K2CO3 and water at room temperature. The methodology worked for a wide range of substrates (22 examples) with up to 83% yield. The protocol is also compatible for gram-scale synthesis.

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