TBHP/TBAI-mediated oxidation of thiophenols for the synthesis of tert-butyl arylsulfinates

被引：9

作者：

Wen, Chunxiao ^{[1
]}

Wu, Jiawei ^{[1
]}

Ou, Yingcong ^{[1
]}

Huang, Yulin ^{[1
]}

Zhang, Kun ^{[1
]}

Chen, Qian ^{[1
]}

机构：

[1] Guangdong Univ Technol, Sch Chem Engn & Light Ind, Guangzhou 510006, Guangdong, Peoples R China

来源：

TETRAHEDRON LETTERS | 2018年 / 59卷 / 40期

关键词：

Thiophenols; Oxidation; Arylsulfinates; TBHP; TBAI; ASYMMETRIC-SYNTHESIS; CHEMICAL-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; SULFINATE ESTERS; ALCOHOLS; EFFICIENT; SULFONAMIDES; HYDRAZIDES; SULFOXIDES; LIGATION;

D O I：

10.1016/j.tetlet.2018.08.048

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel and efficient TBHP/TBAI-mediated oxidation of thiophenols is described. The reactions proceeded smoothly to give tert-butyl arylsulfinates in up to 82% yield with good functional group compatibility under mild conditions. (C) 2018 Elsevier Ltd. All rights reserved.

引用

页码：3609 / 3611

页数：3

共 40 条

[1] The use of two optically active N-sulfinyl α-imino esters in the stereoselective aza-Diels-Alder reaction [J].

Andreassen, Trygve ;

Lorentzen, Marianne ;

Hansen, Lars-Kristian ;

Gautun, Odd R. .

TETRAHEDRON, 2009, 65 (14) :2806-2817

[2] APPLICATIONS OF SULFOXIDES TO ASYMMETRIC-SYNTHESIS OF BIOLOGICALLY-ACTIVE COMPOUNDS [J].

CARRENO, MC .

CHEMICAL REVIEWS, 1995, 95 (06) :1717-1760

[3] Lewis Acid Promoted Diastereoselective Addition of TMSCN and TMSCF3 to Isatin-Derived N-Sulfinyl Ketimines: Synthesis of Optically Active Tetrasubstituted 3-Aminooxindoles [J].

Chen, Diao ;

Xu, Ming-Hua .

JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (16) :7746-7751

[4] Cs2CO3-promoted methylene insertion into disulfide bonds using acetone as a methylene source [J].

Chen, Qian ;

Yu, Guodian ;

Wang, Xiaofeng ;

Huang, Yulin ;

Yan, Yan ;

Huo, Yanping .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (22) :4086-4089

[5] Metal-free NaI/TBHP-mediated sulfonylation of thiols with sulfonyl hydrazides [J].

Chen, Qian ;

Huang, Yulin ;

Wang, Xiaofeng ;

Wu, Jiawei ;

Yu, Guodian .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (10) :1713-1719

[6] Cs2CO3-promoted carbon-sulfur bond construction via cross dehydrogenative coupling of thiophenols with acetonitrile [J].

Chen, Qian ;

Huang, Yulin ;

Wang, Xiaofeng ;

Wen, Chunxiao ;

Yan, Xinxing ;

Zeng, Jiekun .

TETRAHEDRON LETTERS, 2017, 58 (41) :3928-3931

[7] Cs2CO3-promoted cross-dehydrogenative coupling of thiophenols with active methylene compounds [J].

Chen, Qian ;

Wang, Xiaofeng ;

Wen, Chunxiao ;

Huang, Yulin ;

Yan, Xinxing ;

Zeng, Jiekun .

RSC ADVANCES, 2017, 7 (63) :39758-39761

[8] Contra-Friedel-Crafts tert-butylation of substituted aromatic rings via directed metallation and sulfinylation [J].

Clayden, J ;

Stimson, CC ;

Keenan, M .

CHEMICAL COMMUNICATIONS, 2006, (13) :1393-1394

[9] Copper-Catalyzed Oxidative Reaction of -Keto Sulfones with Alcohols via C-S Bond Cleavage: Reaction Development and Mechanism Study [J].

Du, Bingnan ;

Wang, Wenmin ;

Wang, Yang ;

Qi, Zhenghang ;

Tian, Jiaqi ;

Zhou, Jie ;

Wang, Xiaochen ;

Han, Jianlin ;

Ma, Jing ;

Pan, Yi .

CHEMISTRY-AN ASIAN JOURNAL, 2018, 13 (04) :404-408

[10] Copper-Catalyzed Aerobic Oxidative Reaction of Sulfonyl Hydrazides with Alcohols: An Easy Access to Sulfinates [J].

Du, Bingnan ;

Li, Zan ;

Qian, Ping ;

Han, Jianlin ;

Pan, Yi .

CHEMISTRY-AN ASIAN JOURNAL, 2016, 11 (04) :478-481

← 1 2 3 4 →