Bronsted Acid Promoted Sulfonylation of Propargylic Alcohols: Synthesis of Triaryl Allenyl Sulfones under Mild Conditions

被引：2

作者：

Jiang, Shimin ^{[1
]}

Du, Sha ^{[1
]}

Yang, Ruchun ^{[1
]}

Jin, Fengyan ^{[1
]}

Zhou, Zhao-Zhao ^{[2
]}

Tian, Wan-Fa ^{[1
]}

Song, Xian-Rong ^{[1
]}

Xiao, Qiang ^{[1
]}

机构：

[1] Jiangxi Sci & Technol Normal Univ, Inst Organ Chem, Nanchang 330013, Jiangxi, Peoples R China

[2] Nanchang Normal Univ, Coll Chem & Food Sci, Nanchang 330000, Jiangxi, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 26卷 / 03期

基金：

美国国家科学基金会;

关键词：

allenyl sulfones; propargylic alcohols; sodium sulfinates; sulfonylation; synthetic methods; CATALYZED REACTIONS; SULFINATE ESTERS; REARRANGEMENT; EFFICIENT; ISOMERIZATION; CYCLIZATION; ACCESS; AZIDES;

D O I：

10.1002/ejoc.202201377

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient and practical approach for the synthesis of triaryl allenyl sulfones from easily accessible propargylic alcohols was developed, by using sodium sulfinates as a sulfonyl source in the presence of Bronsted acid. The reaction proceeded via allenyl carbocation as the key intermediate and was followed by a nucleophilic attack of sodium sulfinates to produce allenyl sulfones in moderate to excellent yields.

引用

页数：5

共 50 条

[1] Sulfonylation of Propargyl Alcohols with Sulfinamides for the Synthesis of Allenyl Sulfones
Zou, Fei-Fei
Luo, Zhen
Yang, Yu-Ting
Zhuang, Xin
Hong, Chuan-Ming
Liu, Zheng-Qiang
Li, Wan-Fang
Li, Qing-Hua
Liu, Tang-Lin
JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (22): : 15061 - 15070
[2] Silver(I)-Promoted Radical Sulfonylation of Allyl/Propargyl Alcohols: Efficient Synthesis of γ-Keto Sulfones
Fang, Guichun
Liu, Jianquan
Shang, Weidong
Liu, Qun
Bi, Xihe
CHEMISTRY-AN ASIAN JOURNAL, 2016, 11 (23) : 3334 - 3338
[3] Direct and efficient synthesis of tetrasubstituted allenyl organothiophosphates from propargylic alcohols under catalyst- and additive-free conditions
Zhang, Yuxing
Du, Sha
Yang, Tao
Jin, Fengyan
Zhou, Jingyi
Cao, Banpeng
Mao, Zhi-Jie
Song, Xian-Rong
Xiao, Qiang
ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (12) : 3156 - 3162
[4] Facile Synthesis of Fully Substituted Dihydro-β-carbolines via Bronsted Acid Promoted Cascade Reactions of α-Indolyl Propargylic Alcohols with Nitrones
Wang, Lu
Xie, Xin
Liu, Yuanhong
ORGANIC LETTERS, 2012, 14 (23) : 5848 - 5851
[5] A simple and efficient method for sulfonylation of amines, alcohols and phenols with cupric oxide under mild conditions
Meshram, G. A.
Patil, Vishvanath D.
TETRAHEDRON LETTERS, 2009, 50 (10) : 1117 - 1121
[6] An Efficient Method for Sulfonylation of Amines, Alcohols and Phenols with N-Fluorobenzenesulfonimide Under Mild Conditions
Jing Li
Yu Xinling
Guan Mei
Wu Xiaohua
Wang Qiantao
Wu Yong
CHEMICAL RESEARCH IN CHINESE UNIVERSITIES, 2018, 34 (02) : 191 - 196
[7] An Efficient Method for Sulfonylation of Amines, Alcohols and Phenols with N-Fluorobenzenesulfonimide Under Mild Conditions
Li Jing
Xinling Yu
Mei Guan
Xiaohua Wu
Qiantao Wang
Yong Wu
Chemical Research in Chinese Universities, 2018, 34 : 191 - 196
[8] AN IMPROVEMENT IN THE WITTIG-HORNER SYNTHESIS OF ALLENYL SULFONES AND ALLENE CARBOXANILIDES UNDER SONOCHEMICAL CONDITIONS
FILLION, H
REFOUVELET, B
PERA, MH
DUFAUD, V
LUCHE, JL
SYNTHETIC COMMUNICATIONS, 1989, 19 (19) : 3343 - 3348
[9] Asymmetric synthesis of propargylic alcohols via aldol reaction of aldehydes with ynals promoted by prolinol ether-transition metal-Bronsted acid cooperative catalysis
Gomez-Bengoa, Enrique
Garcia, Jesus M.
Jimenez, Sandra
Lapuerta, Irati
Mielgo, Antonia
Odriozola, Jose M.
Otazo, Itziar
Razkin, Jesus
Urruzuno, Inaki
Vera, Silvia
Oiarbide, Mikel
Palomo, Claudio
CHEMICAL SCIENCE, 2013, 4 (08) : 3198 - 3204
[10] Visible-Light Induced Sulfonylation of Nitroolefins for the Synthesis of Vinyl Sulfones under Photocatalyst Free Conditions
Chen, Demao
Sun, Yuanyuan
Dong, Daoqing
Han, Qingqing
Wang, Zuli
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2020, 40 (12) : 4267 - 4273

← 1 2 3 4 5 →