Iodine‐Catalyzed Intramolecular Oxidative Thiolation of Vinylic Carbon‐Hydrogen Bonds via Tandem Iodocyclization and Dehydroiodination: Construction of 2‐Methylene‐3‐thiophenones. Issue 4 (3rd March 2014)

• Record Type: Journal Article
• Authors: Zheng, Gang; Ma, Xiaoli; Liu, Bangyu; Dong, Ying; Wang, Mang
• Is Part Of: Advanced synthesis & catalysis. Volume 356:Issue 4(2014)
• Page Start: 743
• Page End: 748
• Publication Date: 2014-03-03
• Subjects: Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201300815
• Languages: English
• ISSNs: 1615-4150

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>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 <italic>via</italic> tandem iodocyclization and dehydroiodination. The synthetic strategy can also be extended to the cyclization of <italic>ortho</italic>‐methylthiophenyl vinyl ketones leading to 2‐methylene‐3‐benzothiophenones.</p> <p> <boxed-text content-type="graphic" position="anchor" orientation="portrait"> <graphic position="anchor" mimetype="image" xlink:href="ark:/27927/pgg4sx5zrx9" orientation="portrait" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink" /> </boxed-text> </p> </abstract>