Iron(III)-Catalyzed Radical Cross-Coupling of Thiols with Sodium Sulfinates: A Facile Access to Thiosulfonates

被引：24

作者：

Keshari, Twinkle ^{[1
]}

Kapoorr, Ritu ^{[1
]}

Yadav, Lal Dhar S. ^{[1
]}

机构：

[1] Univ Allahabad, Dept Chem, Green Synth Lab, Allahabad 211002, Uttar Pradesh, India

来源：

SYNLETT | 2016年 / 27卷 / 12期

关键词：

sulfonates; thiols; thiosulfonates; iron; catalysis; oxidation; AEROBIC ALCOHOL OXIDATIONS; BETA-KETO SULFONES; SELECTIVE OXIDATION; MOLECULAR-OXYGEN; BOND FORMATION; DINITROGEN TETROXIDE; DIOXYGEN ACTIVATION; S-ESTERS; CORRESPONDING THIOLSULFONATES; CHARCOAL N2O4/CHARCOAL;

D O I：

10.1055/s-0035-1562101

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A convenient and efficient synthesis of symmetrical and asymmetric thiosulfonates from thiols and sodium sulfinates is reported. The protocol involves iron(III)-catalyzed formation of sulfenyl and sulfonyl radicals in situ under aerobic conditions and their subsequent cross-coupling to afford thiosulfonates in 83-96% yield. The utilization of readily available, nontoxic, and inexpensive iron(III) as a catalyst and atmospheric oxygen as an oxidant is within the confines of green and sustainable chemistry.

引用

页码：1878 / 1882

页数：5

共 94 条

[11]

BOLDYREV BG, 1987, ZH ORG KHIM+, V23, P1878

[12] CAN/I2-catalyzed Chemoselective Synthesis of Thiosulfonates by Oxidation of Disulfides or Thiols [J].

Cai, Ming-Tiao ;

Lv, Guang-Shu ;

Chen, Jiu-Xi ;

Gao, Wen-Xia ;

Ding, Jin-Chang ;

Wu, Hua-Yue .

CHEMISTRY LETTERS, 2010, 39 (04) :368-369

[13]

Chandra Mohan D., 2013, J ORG CHEM, V78, P1266

[14] Chemistry of acyl radicals [J].

Chatgilialoglu, C ;

Crich, D ;

Komatsu, M ;

Ryu, I .

CHEMICAL REVIEWS, 1999, 99 (08) :1991-2069

[15] SEARCH FOR AN ALPHA-DISULFOXIDE AS AN INTERMEDIATE IN OXIDATION OF AN ARYL THIOLSULFINATE [J].

CHAU, MM ;

KICE, JL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (24) :7711-7716

[16] K2S2O8-Mediated Aerobic Oxysulfonylation of Olefins into β-Keto Sulfones in Aqueous Media [J].

Chawla, Ruchi ;

Singh, Atul K. ;

Yadav, Lal Dhar S. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (10) :2032-2036

[17] Copper-Catalyzed Synthesis of Azaspirocyclohexadienones from α-Azido-N-arylamides under an Oxygen Atmosphere [J].

Chiba, Shunsuke ;

Zhang, Line ;

Lee, Jian-Yuan .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (21) :7266-+

[18] THIOSULFONATE PREPARATION BY THE THIOSULFINATE SULFINIC ACID REACTION [J].

CLARKE, V ;

COLE, ER .

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1994, 90 (1-4) :171-173

[19]

Curran D.P., 1996, Stereochemistry of Radical Reactions

[20] Adventures in sulfur-nitrogen [J].

Davis, Franklin A. .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (24) :8993-9003

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