4.6 Article

Catalyst-free chemoselective α-sulfenylation/β-thiolation for α,β-unsaturated carbonyl compounds

期刊

RSC ADVANCES
卷 9, 期 45, 页码 26419-26424

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ROYAL SOC CHEMISTRY
DOI: 10.1039/c9ra05708k

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资金

  1. National Natural Science Foundation of China [21572060]
  2. National Key Research and Development Plan [2017YFD0200504]

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A novel, efficient, catalyst-free and product-controllable strategy has been developed for the chemoselective alpha-sulfenylation/beta-thiolation of alpha,beta-unsaturated carbonyl compounds. An aromatic sulfur group could be chemoselectively introduced at alpha- or beta-position of carbonyls with different sulfur reagents under slightly changed reaction conditions. A series of desired products were obtained in moderate to excellent yields. Mechanistic studies revealed that B(2)pin(2) played the key role in activating the transformation towards the beta-thiolation of alpha,beta-unsaturated carbonyl compounds. This transition-metal-catalyst-free method provides a convenient and efficient tool for the highly chemoselective preparation of alpha-thiolation or beta-sulfenylation products of alpha,beta-unsaturated carbonyl compounds.

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