4-SULFANYLBENZENE-1,3-DIOL

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CAS: 2553-70-0
MF: C6H6O2S
MW: 142.17564
Synonyms: 4-SULFANYLBENZENE-1,3-DIOL

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Scott J. Miller

Yale University
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Co-reporter: Philipp S. Selig, Scott J. Miller
pp: 2148-2151
Publication Date(Web):27 April 2011
DOI: 10.1016/j.tetlet.2010.11.077
ortho-Mercaptobenzoic acid and ortho-mercaptophenols were discovered as efficient thiol catalysts of both the intramolecular Morita–Baylis–Hillman (MBH) and Rauhut–Currier (RC) reaction. High reaction rates were achieved under mildly basic, aqueous conditions. The unprecedented catalytic activity of these protic nucleophiles could originate from a Brønsted acid induced destabilization of intermediate thioethers and thus represent a unique mechanism of multifunctional Lewis base catalysis.Image for unlabelled figure