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

[41] MILD AND EFFICIENT CHEMOSELECTIVE TETRAHYDROPYRANYLATION OF ALCOHOLS USING BRONSTED ACIDIC IONIC LIQUID AS CATALYST UNDER SOLVENT-FREE CONDITIONS
Hajipour, Abdol R.
Nasresfahani, Zahra
SYNTHETIC COMMUNICATIONS, 2012, 42 (13) : 1995 - 2006
[42] Bronsted acid-catalyzed synthesis of diarylmethanes under non-genotoxic conditions
Mendoza, Oscar
Rossey, Guy
Ghosez, Leon
TETRAHEDRON LETTERS, 2011, 52 (17) : 2235 - 2239
[43] One-Pot Synthesis of Allylic Sulfones, Ketosulfones, and Triflyl Allylic Alcohols from Domino Reactions of Allylic Alcohols with Sulfinic Acid under Metal-Free Conditions
Chu, Xue-Qiang
Meng, Hua
Xu, Xiao-Ping
Ji, Shun-Jun
CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (32) : 11359 - 11368
[44] Lewis acid-promoted transesterification of N-acyl oxazolidinones under mild conditions
Orita, A
Nagano, Y
Hirano, J
Otera, J
SYNLETT, 2001, (05) : 637 - 639
[45] Indole synthesis from N-allenyl-2-iodoanilines under mild conditions mediated by samarium(II) diiodide
Iwasaki, Hiroki
Suzuki, Kenji
Yamane, Mitsunari
Yoshida, Shohei
Kojima, Naoto
Ozeki, Minoru
Yamashita, Masayuki
ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (35) : 6812 - 6815
[46] A conjugate Lewis base-Bronsted acid catalyst for the sulfenylation of nitrogen containing heterocycles under mild conditions
Nalbandian, Christopher J.
Miller, Eric M.
Toenjes, Sean T.
Gustafson, Jeffery L.
CHEMICAL COMMUNICATIONS, 2017, 53 (09) : 1494 - 1497
[47] N-Chlorosuccinimide-promoted synthesis of thiophosphates from thiols and phosphonates under mild conditions
Liu, Yi-Chen
Lee, Chin-Fa
GREEN CHEMISTRY, 2014, 16 (01) : 357 - 364
[48] Electrochemically promoted synthesis of polysubstituted oxazoles from β-diketone derivatives and benzylamines under mild conditions
Yuan, Gaoqing
Zhu, Zechen
Gao, Xiaofang
Jiang, Huanfeng
RSC ADVANCES, 2014, 4 (46): : 24300 - 24303
[49] Practical and general method for direct synthesis of alkyl fluorides from alcohols under mild conditions
Bandgar, BP
Kamble, VT
Biradar, AV
MONATSHEFTE FUR CHEMIE, 2005, 136 (09): : 1579 - 1582
[50] Practical and General Method for Direct Synthesis of Alkyl Fluorides from Alcohols under Mild Conditions
Babasaheb P. Bandgar
Vinod T. Kamble
Ankush V. Biradar
Monatshefte für Chemie / Chemical Monthly, 2005, 136 : 1579 - 1582

← 1 2 3 4 5 →