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硅氧基甲亚磺酸盐作为用于砜和磺酰基衍生物模块化合成的亚磺酸盐等价物。

Silyloxymethanesulfinate as a sulfoxylate equivalent for the modular synthesis of sulfones and sulfonyl derivatives.

作者信息

Kim Dae-Kwon, Um Hyun-Suk, Park Hoyoon, Kim Seonwoo, Choi Jin, Lee Chulbom

机构信息

Department of Chemistry, Seoul National University Seoul 08826 Republic of Korea

出版信息

Chem Sci. 2020 Oct 22;11(48):13071-13078. doi: 10.1039/d0sc02947e.

DOI:10.1039/d0sc02947e
PMID:34094489
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8163199/
Abstract

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.

摘要

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。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ce3f/8163199/3ae742612118/d0sc02947e-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ce3f/8163199/330ea55031bb/d0sc02947e-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ce3f/8163199/6ed38142848b/d0sc02947e-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ce3f/8163199/3ae742612118/d0sc02947e-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ce3f/8163199/330ea55031bb/d0sc02947e-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ce3f/8163199/6ed38142848b/d0sc02947e-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ce3f/8163199/3ae742612118/d0sc02947e-s3.jpg

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