NaHSO3-Mediated Direct Synthesis of Sulfinic Esters from Sulfonyl Hydrazides under Transition-Metal-Free Conditions

被引：13

作者：

Zhang, Guofu ^{[1
]}

Fan, Qiankun ^{[1
]}

Wang, Huimin ^{[1
]}

Zhao, Yiyong ^{[2
]}

Ding, Chengrong ^{[1
]}

机构：

[1] Zhejiang Univ Technol, Coll Chem Engn, Hangzhou 310014, Peoples R China

[2] Zhejiang Ecol Environm Low Carbon Dev Ctr, Hangzhou 310012, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2021年 / 363卷 / 03期

基金：

中国国家自然科学基金;

关键词：

sulfonyl hydrazides; alcohols; sulfinic esters; transition-metal-free; radical pathway; ONE-POT SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; ARENESULFONYL CHLORIDES; EFFICIENT; ALKENES;

D O I：

10.1002/adsc.202001202

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

We have developed a protocol for the NaHSO3-promoted esterification of sulfonyl hydrazides with alcohols for the synthesis of sulfinic esters. Various sulfonyl hydrazides could be converted to the corresponding sulfinic esters in good to high yields. The merits of this protocol include mild transition-metal-free reaction conditions, an inexpensive and available reagent, and operational simplicity. Controlled experiments reveal that this transformation probably undergoes via a radical pathway.

引用

页码：833 / 837

页数：5

共 50 条

[11] Direct Conversion of Haloarenes to Phenols under Mild, Transition-Metal-Free Conditions
Fier, Patrick S.
Maloney, Kevin M.
ORGANIC LETTERS, 2016, 18 (09) : 2244 - 2247
[12] Transition-Metal-Free Direct Trifluoromethylation and Perfluoroalkylation of Imidazopyridines under Mild Conditions
Han, Shuaijun
Gao, Xianying
Wu, Qingsong
Li, Jingya
Zou, Dapeng
Wu, Yangjie
Wu, Yusheng
ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (07) : 1559 - 1563
[13] TEMPO and its derivatives mediated reactions under transition-metal-free conditions
Zhuang, Hongfeng
Li, Heng
Zhang, Shuai
Yin, Yanbin
Han, Feng
Sun, Chao
Miao, Chengxia
CHINESE CHEMICAL LETTERS, 2020, 31 (01) : 39 - 48
[14] Borate-mediated aryl polyfluoroalkoxylation under transition-metal-free conditions
Kikushima, Kotaro
Tsuda, Tomoka
Miyamoto, Naoki
Kita, Yasuyuki
Dohi, Toshifumi
CHEMICAL COMMUNICATIONS, 2024, 60 (76) : 10552 - 10555
[15] Transition-Metal-Free Radical-Triggered Hydrosulfonylation and Disulfonylation Reaction of Substituted Maleimides with Sulfonyl Hydrazides
Ruan, Hong-Li
Ma, Yi-Lin
Man, Ke-Xin
Zhao, Sheng-Yin
JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (05): : 3762 - 3769
[16] Synthesis of phenothiazines from cyclohexanones and 2-aminobenzenethiols under transition-metal-free conditions
Liao, Yunfeng
Jiang, Pengcheng
Chen, Shanping
Xiao, Fuhong
Deng, Guo-Jun
RSC ADVANCES, 2013, 3 (40): : 18605 - 18608
[17] Visible-Light-Mediated ipso -Carbosulfonylation of Alkynes: Synthesis of 3-Sulfonylspiro[4,5]trienones from Propiolamides and Sulfonyl Chlorides under Transition-Metal-Free Conditions
Liu, Yu
Wang, Qiao-Lin
Xiong, Bi-Quan
Zhang, Pan-Liang
Yang, Chang-An
Gong, Yan-Xia
Liao, Jing
Zhou, Quan
SYNLETT, 2018, 29 (18) : 2396 - 2403
[18] Transition-metal-free Cyclization of Mucohalic Acids with Sulfonyl Hydrazides: An Approach to Pyridazin-3(2H)-ones
Chen, Qi
Li, Huan-Qing
Yang, Kai
Xu, Wen-Jin
Zeng, Yu
Wang, Zhao-Yang
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 12 (11)
[19] Direct Transformation of Methyl Imines to -Iminonitriles under Mild and Transition-Metal-Free Conditions
Chen, Feng
Huang, Xiaoqiang
Cui, Yuxin
Jiao, Ning
CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (34) : 11199 - 11202
[20] A metal-free approach for the synthesis of thiosulfonates from sulfonyl hydrazides
Li, Xue
Liao, WeiBo
Huang, Bin
Zhang, YuanYuan
Wang, JiangWei
JOURNAL OF CHEMICAL RESEARCH, 2021, 45 (11-12) : 921 - 927

← 1 2 3 4 5 →