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Iodine‐Catalyzed Intramolecular Oxidative Thiolation of Vinylic Carbon‐Hydrogen Bonds via Tandem Iodocyclization and Dehydroiodination: Construction of 2‐Methylene‐3‐thiophenones
Author(s) -
Zheng Gang,
Ma Xiaoli,
Liu Bangyu,
Dong Ying,
Wang Mang
Publication year - 2014
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201300815
Subject(s) - chemistry , methylene , ketene , tandem , intramolecular force , catalysis , medicinal chemistry , iodine , selectivity , organic chemistry , materials science , composite material
A metal‐free vinylic carbon‐hydrogen bond thiolation has been developed. Under the catalysis of iodine (10 mol%), the cyclization of α‐alkenoyl ketene dithioacetals afforded a broad range of polyfunctionalized 2‐methylene‐3‐thiophenones in good selectivity with moderate to excellent yields via tandem iodocyclization and dehydroiodination. The synthetic strategy can also be extended to the cyclization of ortho ‐methylthiophenyl vinyl ketones leading to 2‐methylene‐3‐benzothiophenones.