4.7 Article

PPh3•HBr-DMSO: A Reagent System for Diverse Chemoselective Transformations

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 80, Issue 12, Pages 6400-6410

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b00846

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Funding

  1. CSIR New Delhi (Network Project) [ORIGIN-CSC0108]
  2. CSIR-India
  3. NIPER-Kolkata
  4. UGC-India

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The broad applicability of the hitherto unexplored reagent combination PPh3 center dot HBr-DMSO is exemplified with multiple highly diverse one-step transformations to synthetically useful building blocks, such as flavones, 4H-thiochromen-4-ones, alpha-hydroxy ketones, 1,4-naphthoquinones (including vitamin K-3), 2-bromo-3-substituted-1H-1-indenones, 2-rnethylthio-1H-1-indenones, 3-butyne-1,2-dione, and 4-pentene-2,3-diones. The simple and mild reaction conditions make the reagent superior in terms of yield and substrate scope in comparison with the existing alternatives.

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