Aliphatic sulfonyl fluoride synthesis via reductive decarboxylative fluorosulfonylation of aliphatic carboxylic acid NHPI esters

被引：42

作者：

Ma, Zhanhu ^{[1
]}

Liu, Yongan ^{[2
]}

Ma, Xiaoyu ^{[1
]}

Hu, Xiaojun ^{[1
]}

Guo, Yong ^{[2
]}

Chen, Qing-Yun ^{[2
]}

Liu, Chao ^{[1
,2
]}

机构：

[1] Shanghai Inst Technol, Sch Chem & Environm Engn, 100 Haiquan Rd, Shanghai 201418, Peoples R China

[2] Chinese Acad Sci, Univ Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2022年 / 9卷 / 04期

基金：

中国国家自然科学基金;

关键词：

SUFEX CLICK CHEMISTRY; ONE-POT; REAGENT;

D O I：

10.1039/d1qo01655e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Based on a radical sulfur dioxide insertion and fluorination strategy, we have developed an efficient method for aliphatic sulfonyl fluoride synthesis using abundant carboxylic acids, a reductant, a sulfur dioxide surrogate and the electrophilic fluorination reagent N-fluorobenzenesulfonimide (NFSI) under reduction conditions. This protocol provides a convenient synthetic pathway for various aliphatic sulfonyl fluorides and tolerates a wide range of functional groups.

引用

页码：1115 / 1120

页数：6

共 50 条

[31] Interaction between primary aliphatic amines and carboxylic acid esters in aqueous micellar solutions of cationic surfactants
Mirgorodskaya, AB
Kudryavtseva, LA
Zakharova, LY
Bel'skii, VE
RUSSIAN CHEMICAL BULLETIN, 1998, 47 (07) : 1296 - 1301
[32] KINETIC RELATIONSHIPS OF ACIDOLYSIS OF METHYL-ESTERS OF ALIPHATIC CARBOXYLIC-ACIDS BY ACRYLIC-ACID
CHUBAROV, GA
DANOV, SM
LOGUTOV, VI
OBMELYUKHINA, TN
JOURNAL OF APPLIED CHEMISTRY OF THE USSR, 1984, 57 (06): : 1229 - 1233
[33] RACEMIZATION OF ALPHA-AMINO-ACID ESTERS BY ALIPHATIC-KETONES IN THE PRESENCE OF CARBOXYLIC-ACIDS
BARRY, LG
PUGNIERE, M
CASTRO, B
PREVIERO, A
INTERNATIONAL JOURNAL OF PEPTIDE AND PROTEIN RESEARCH, 1993, 41 (04): : 323 - 325
[34] Interaction between primary aliphatic amines and carboxylic acid esters in aqueous micellar solutions of cationic surfactants
A. B. Mirgorodskaya
L. A. Kudryavtseva
L. Ya. Zakharova
V. E. Bel'skii
Russian Chemical Bulletin, 1998, 47 : 1296 - 1301
[35] HIGH-PRESSURE SYNTHESIS OF ALIPHATIC POLYIMIDES VIA SALT MONOMERS COMPOSED OF ALIPHATIC DIAMINES AND OXYDIPHTHALIC ACID
ITOYA, K
KUMAGAI, Y
KAKIMOTO, MA
IMAI, Y
MACROMOLECULES, 1994, 27 (15) : 4101 - 4105
[36] Selective synthesis of functionalized linear aliphatic primary amines via decarboxylative radical-polar crossover
Cauwenbergh, Robin
Sahoo, Prakash Kumar
Maiti, Rakesh
Mathew, Abra
Kuniyil, Rositha
Das, Shoubhik
GREEN CHEMISTRY, 2024, 26 (01) : 264 - 276
[37] SYNTHESIS AND REACTIVITY OF ACID-CHLORIDES OF ALIPHATIC BETA-(CHLOROSULFINYL)CARBOXYLIC ACIDS
VASILEVA, TP
LINKOVA, MG
KILDISHEVA, OV
KNUNYANTS, IL
BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1981, 30 (01): : 137 - 143
[38] Synthesis and solid state C-13 and F-19 NMR characterization of aliphatic and aromatic carboxylic acid fluoride polymers
Hagaman, EW
Kee, SK
Britt, PF
ANALYTICAL CHEMISTRY, 1997, 69 (19) : 3950 - 3958
[39] Synthesis of γ-Nitro Aliphatic Methyl Esters Via Michael Additions Promoted by Microwave Irradiation
Escalante, Jaime
Diaz-Coutino, Francisco D.
MOLECULES, 2009, 14 (04): : 1595 - 1604
[40] Aliphatic esters of acrylic acid - Kinetic synthesis and present catalyst of esterification process.
Nowak, P
PRZEMYSL CHEMICZNY, 2000, 79 (06): : 186 - +

← 1 2 3 4 5 →