Department of Chemistry, Fudan University, 2005 Songhu Road, Shanghai 200438, China.
Chem Commun (Camb). 2019 Feb 12;55(14):2062-2065. doi: 10.1039/c8cc10246e.
A three-component reaction between 4-substituted Hantzsch esters, DABCO·(SO2)2, and vinyl azides in the presence of photoredox catalysts under visible light irradiation is developed. Substituted Hantzsch esters as radical reservoirs are used in the reaction between sulfur dioxide and vinyl azides. A range of (Z)-2-(alkylsulfonyl)-1-arylethen-1-amines is obtained in moderate to good yields with good regioselectivity and stereoselectivity. The transformation proceeds efficiently under mild conditions with a broad reaction scope. A plausible mechanism is proposed, which involves a radical process with the insertion of sulfur dioxide initiated by an alkyl radical from the 4-substituted Hantzsch ester.
发展了一种在可见光照条件下，光氧化还原催化剂存在下，4-取代的 Hantzsch 酯、DABCO·(SO2)2 和乙烯基叠氮化物之间的三组分反应。在二氧化硫和乙烯基叠氮化物的反应中，使用取代的 Hantzsch 酯作为自由基储库。在温和条件下，以中等到良好的收率、良好的区域选择性和立体选择性得到一系列(Z)-2-(烷基亚磺酰基)-1-芳基乙烯-1-胺。该转化具有广泛的反应范围，反应条件温和，效率高。提出了一种可能的机制，该机制涉及自由基过程，其中 4-取代的 Hantzsch 酯中的烷基自由基引发二氧化硫的插入。
