4.8 Article

Cross-Coupling of Meyer-Schuster Intermediates under Dual Gold Photoredox Catalysis

Journal

ORGANIC LETTERS
Volume 18, Issue 3, Pages 484-487

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.5b03531

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Funding

  1. National Research Foundation of Korea [NRF- 2012M3A7B4049653, NRF-2014-011165]
  2. National Research Foundation of Korea [2014R1A5A1011165, 2012M3A7B4049653] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)

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Under dual gold/photoredox catalytic conditions, intermediates from the Meyer-Schuster rearrangement underwent an efficient cross-coupling with arene diazonium salts, leading to alpha-arylated enones. Diazonium salts assisted the dissociation of the propargyl hydroxyl group by forming alkoxydiazenes in the Meyer-Schuster rearrangement, and the coupling was proposed to proceed through an allenyl methyl ether.

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