Kim Dae-Kwon, Um Hyun-Suk, Park Hoyoon, Kim Seonwoo, Choi Jin, Lee Chulbom
Department of Chemistry, Seoul National University Seoul 08826 Republic of Korea
Chem Sci. 2020 Oct 22;11(48):13071-13078. doi: 10.1039/d0sc02947e.
An efficient protocol for the modular synthesis of sulfones and sulfonyl derivatives has been developed utilizing sodium -butyldimethylsilyloxymethanesulfinate (TBSOMS-Na) as a sulfoxylate (SO ) equivalent. TBSOMS-Na, easily prepared from the commercial reagents Rongalite™ and TBSCl, serves as a potent nucleophile in -alkylation and Cu-catalyzed -arylation reactions with alkyl and aryl electrophiles. The sulfone products thus obtained can undergo the second bond formation at the sulfur center with various electrophiles without a separate unmasking step to afford sulfones and sulfonyl derivatives such as sulfonamides and sulfonyl fluorides.
利用丁基二甲基硅氧基甲烷亚磺酸钠(TBSOMS-Na)作为亚磺酸盐(SO)等价物,已开发出一种用于砜和磺酰基衍生物模块化合成的有效方案。TBSOMS-Na易于由市售试剂雕白粉™和TBSCl制备,在与烷基和芳基亲电试剂的α-烷基化和铜催化的α-芳基化反应中作为强亲核试剂。由此获得的砜产物可在硫中心与各种亲电试剂进行第二次键形成,无需单独的去保护步骤,从而得到砜和磺酰基衍生物,如磺酰胺和磺酰氟。