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三组分磺酰胺合成中的S(vi)：在钯催化的铃木-宫浦偶联反应中使用硫酰氯作为关键试剂

S(vi) in three-component sulfonamide synthesis: use of sulfuric chloride as a linchpin in palladium-catalyzed Suzuki-Miyaura coupling.

作者信息

Wang Xuefeng, Yang Min, Ye Shengqing, Kuang Yunyan, Wu Jie

机构信息

School of Pharmaceutical and Materials Engineering, Institute for Advanced Studies, Taizhou University 1139 Shifu Avenue Taizhou 318000 China

Department of Chemistry, Fudan University 2005 Songhu Road Shanghai 200438 China.

出版信息

Chem Sci. 2021 Apr 6;12(18):6437-6441. doi: 10.1039/d1sc01351c.

DOI:10.1039/d1sc01351c
PMID:34084444
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8115270/
Abstract

Sulfuric chloride is used as the source of the -SO- group in a palladium-catalyzed three-component synthesis of sulfonamides. Suzuki-Miyaura coupling between the generated sulfamoyl chlorides and boronic acids gives rise to diverse sulfonamides in moderate to high yields with excellent reaction selectivity. Although this transformation is not workable for primary amines or anilines, the results show high functional group tolerance. With the solving of the desulfonylation problem and utilization of cheap and easily accessible sulfuric chloride as the source of sulfur dioxide, redox-neutral three-component synthesis of sulfonamides is first achieved.

摘要

在钯催化的磺酰胺三组分合成中，硫酰氯用作-SO-基团的来源。生成的磺酰氯与硼酸之间的铃木-宫浦偶联反应能以中等到高的产率、优异的反应选择性得到多种磺酰胺。尽管这种转化对于伯胺或苯胺不可行，但结果显示出对官能团的高耐受性。随着脱磺酰化问题的解决以及使用廉价且易于获得的硫酰氯作为二氧化硫的来源，首次实现了磺酰胺的氧化还原中性三组分合成。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f92d/8115270/e2405b7c7ed0/d1sc01351c-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f92d/8115270/c0b70ec533e3/d1sc01351c-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f92d/8115270/d71321008500/d1sc01351c-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f92d/8115270/50e79d8ed1b7/d1sc01351c-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f92d/8115270/e2405b7c7ed0/d1sc01351c-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f92d/8115270/c0b70ec533e3/d1sc01351c-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f92d/8115270/d71321008500/d1sc01351c-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f92d/8115270/50e79d8ed1b7/d1sc01351c-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f92d/8115270/e2405b7c7ed0/d1sc01351c-s4.jpg

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