Cai Zhongliang, Yao Zhi, Jiang Liqin
School of Chemistry and Molecular Engineering, East China Normal University, 500 Dongchuan Road, Shanghai 200241, China.
Org Lett. 2021 Jan 15;23(2):311-316. doi: 10.1021/acs.orglett.0c03796. Epub 2021 Jan 6.
,-Disubstituted thioamides coupled with -tosylhydrazones under Pd(TFA)/BuXPhos catalyst and NaOBu, and the intermediates from palladium carbene migratory insertion containing hydrogen were trapped by intramolecular esters activated by BF·EtO instead of undergoing H elimination, providing polyfunctional thiophen-3()-ones with sulfur-containing tetrasubstituted carbon centers in moderate to good yields. The reaction features the formation of three bonds in a single operation, odorless, safe, and easily available substrates, wide substrate scope, and excellent functional group tolerance.
在钯（三氟乙酸盐）/双（二叔丁基膦）联苯催化剂和叔丁醇钠的作用下，α，α-二取代硫代酰胺与α-甲苯磺酰腙发生偶联反应，由钯卡宾迁移插入产生的含氢中间体被三氟化硼乙醚活化的分子内酯捕获，而非发生氢消除反应，从而以中等至良好的产率提供具有含硫四取代碳中心的多官能团噻吩-3（2H）-酮。该反应的特点是在一步操作中形成三根键、底物无味、安全且易于获得、底物范围广泛以及对官能团具有出色的耐受性。
