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A Brønsted acid-catalyzed 1,4-addition hydrothiolation of branched 1,3-dienes was explored for the first time. A solvent-controlled divergent synthesis of sulfides is also disclosed. Use of acetonitrile as a solvent gave… Click to show full abstract
A Brønsted acid-catalyzed 1,4-addition hydrothiolation of branched 1,3-dienes was explored for the first time. A solvent-controlled divergent synthesis of sulfides is also disclosed. Use of acetonitrile as a solvent gave allylic sulfides as hydrothiolation products, while thiochromane derivatives (hydrothiolation/Friedel-Crafts products) were obtained using dichloromethane as the solvent. The origin of the regioselectivity of hydrothiolation was explored through density functional theory calculations.
Journal Title: Organic letters
Year Published: 2021
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