ortho-Acidic aromatic thiols as efficient catalysts of intramolecular Morita-Baylis-Hillman and Rauhut-Currier reactions

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 Bronsted acid induced destabilization of intermediate thioethers and thus represent a unique mechanism of multifunctional Lewis base catalysis. (C) 2010 Elsevier Ltd. All rights reserved.