Synthesis of Sulfonyl Fluorides from Sulfonamides

被引：57

作者：

Perez-Palau, Marina ^{[1
]}

Cornella, Josep ^{[1
]}

机构：

[1] Max Planck Inst Kohlenforsch, Kaiser Wilhelm Pl 1, Mulheim 45470, Germany

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 2020卷 / 17期

关键词：

Fluorine; Late-stage modification; Pyrylium reagents; Sulfonamides; Sulfonyl fluorides; Synthetic methods; IRREVERSIBLE ENZYME-INHIBITORS; XANTHINE-OXIDASE; CONVENIENT; PROBES; SUFEX;

D O I：

10.1002/ejoc.202000022

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple and practical synthesis of sulfonyl fluorides from sulfonamides is reported. The method capitalizes on the formation of the sulfonyl chloride by virtue of the reaction of Pyry-BF4 and MgCl2, and subsequent in situ conversion to the more robust and stable sulfonyl fluoride by the presence of KF. The mild conditions and high chemoselectivity of the protocol enable the late-stage formation of sulfonyl fluorides from densely functionalized molecules.

引用

页码：2497 / 2500

页数：4

共 50 条

[1] Lewis acid mediated synthesis of sulfonamides from sulfonyl fluorides
Woroch, Cristian
Rusznak, Mark
Ende, Christopher Am
Mukherjee, Paramita
Franzese, Ryan
Etuk, Sarah
Kwan, Sabrina
Ball, Nicholas
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 255
[2] Sulfonyl Fluorides as Alternative to Sulfonyl Chlorides in Parallel Synthesis of Aliphatic Sulfonamides
Bogolubsky, Andrey V.
Moroz, Yurii S.
Mykhailiuk, Pavel K.
Pipko, Sergey E.
Konovets, Anzhelika I.
Sadkova, Irina V.
Tolmachev, Andrey
ACS COMBINATORIAL SCIENCE, 2014, 16 (04) : 192 - 197
[3] Electrochemical synthesis of sulfonyl fluorides from sulfonyl hydrazides
Park, Jin Kyu
Oh, Jonghoon
Lee, Sunwoo
ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (13) : 3407 - 3413
[4] A convenient preparation of heteroaryl sulfonamides and sulfonyl fluorides from heteroaryl thiols
Wright, SW
Hallstrom, KN
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (03): : 1080 - 1084
[5] Lewis acid activation of sulfonyl fluorides to form sulfonamides
Mukherjee, Paramita
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 256
[6] Efficient synthesis of sulfonyl azides from sulfonamides
Raushel, Jessica
Pitram, Suresh M.
Fokin, Valery V.
ORGANIC LETTERS, 2008, 10 (16) : 3385 - 3388
[7] Facile synthesis of sulfonyl fluorides
Dong, Jiajia
Sharpless, K. Barry
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 243
[8] Facile synthesis of sulfonyl fluorides from sulfonic acids
Thomson, Brodie J.
Khasnavis, Samuel R.
Grigorian, Emma C.
Krishnan, Rohun
Yassa, Theodore D.
Lee, Kelvin
Sammis, Glenn M.
Ball, Nicholas D.
CHEMICAL COMMUNICATIONS, 2023, 59 (05) : 555 - 558
[9] SYNTHESIS OF SULFONES FROM SULFONYL FLUORIDES AND ORGANOMETALLIC COMPOUNDS
KHODAIR, AI
ABDELWAHAB, AA
ELKHAWAGA, AM
ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 1978, 33 (04): : 403 - 406
[10] Direct Synthesis Sulfonamides from Nitroarenes and Sulfonyl Chlorides in Water
Yue, Huilan
Bao, Pengli
Wang, Leilei
Lu, Xiaoxia
Yang, Daoshan
Wang, Hua
Wei, Wei
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2019, 39 (02) : 463 - 468

← 1 2 3 4 5 →