Castoldi Laura, Di Tommaso Ester Maria, Reitti Marcus, Gräfen Barbara, Olofsson Berit
Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, 10691, Stockholm, Sweden.
Angew Chem Int Ed Engl. 2020 Sep 1;59(36):15512-15516. doi: 10.1002/anie.202002936. Epub 2020 Jun 15.
The iodine(III) reagents vinylbenziodoxolones (VBX) were employed to vinylate a series of aliphatic and aromatic thiols, providing E-alkenyl sulfides with complete chemo- and regioselectivity, as well as excellent stereoselectivity. The methodology displays high functional group tolerance and proceeds under mild and transition metal-free conditions without the need for excess substrate or reagents. Mercaptothiazoles could be vinylated under modified conditions, resulting in opposite stereoselectivity compared to previous reactions with vinyliodonium salts. Novel VBX reagents with substituted benziodoxolone cores were prepared, and improved reactivity was discovered with a dimethyl-substituted core.
碘（III）试剂乙烯基苯并碘恶唑酮（VBX）用于使一系列脂肪族和芳香族硫醇乙烯基化，以完全的化学和区域选择性以及优异的立体选择性提供E-烯基硫醚。该方法具有高官能团耐受性，在温和且无过渡金属的条件下进行，无需过量的底物或试剂。巯基噻唑在改良条件下可以乙烯基化，与之前与乙烯基碘鎓盐的反应相比，立体选择性相反。制备了具有取代苯并碘恶唑酮核心的新型VBX试剂，并发现二甲基取代的核心具有更高的反应活性。
