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

[41]

Kutsyuba T. S., 1997, THEOR EXP CHEM, V33, P26

[42] Reactivity of dioxygen-copper systems [J].

Lewis, EA ;

Tolman, WB .

CHEMICAL REVIEWS, 2004, 104 (02) :1047-1076

[43] Modern synthetic methods for copper-mediated C(aryl)-O, C(aryl)-N, and C(aryl)-S bond formation [J].

Ley, SV ;

Thomas, AW .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (44) :5400-5449

[44] Iron-catalyzed selective oxidation of sulfides to sulfoxides with the polyethylene glycol/O2 system [J].

Li, Bin ;

Liu, An-Hua ;

He, Liang-Nian ;

Yang, Zhen-Zhen ;

Gao, Jian ;

Chen, Kai-Hong .

GREEN CHEMISTRY, 2012, 14 (01) :130-135

[45] Sc(OTf)3-catalyzed synthesis of thiosulfonates in ionic liquid-water [J].

Liang, Gaigai ;

Chen, Jing ;

Chen, Jiali ;

Li, Wanmei ;

Chen, Jiuxi ;

Wu, Huayue .

TETRAHEDRON LETTERS, 2012, 53 (50) :6768-6770

[46] NBS-Promoted Sulfenylation of Sulfinates with Disulfides Leading to Unsymmetrical or Symmetrical Thiosulfonates [J].

Liang Gaigai ;

Liu Miaochang ;

Chen Jiuxi ;

Ding Jinchang ;

Gao Wenxia ;

Wu Huayue .

CHINESE JOURNAL OF CHEMISTRY, 2012, 30 (07) :1611-1616

[47] Temperature-controlled selective reduction of arenesulfonyl chlorides promoted by samarium metal in DMF [J].

Liu, YJ ;

Zhang, YM .

TETRAHEDRON LETTERS, 2003, 44 (22) :4291-4294

[48] Dioxygen-Triggered Oxidative Radical Reaction: Direct Aerobic Difunctionalization of Terminal Alkynes toward β-Keto Sulfones [J].

Lu, Qingquan ;

Zhang, Jian ;

Zhao, Ganglu ;

Qi, Yue ;

Wang, Huamin ;

Lei, Aiwen .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (31) :11481-11484

[49] Aerobic Oxysulfonylation of Alkenes Leading to Secondary and Tertiary β-Hydroxysulfones [J].

Lu, Qingquan ;

Zhang, Jian ;

Wei, Fuliang ;

Qi, Yue ;

Wang, Huamin ;

Liu, Zhiliang ;

Lei, Aiwen .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (28) :7156-7159

[50] Unexpected differences in the α-halogenation and related reactivity of sulfones with perhaloalkanes in KOH-t-BuOH [J].

Meyers, CY ;

Roch, CYK ;

Hua, DH ;

Kolb, VM ;

Matthews, WS ;

Parady, TE ;

Horii, T ;

Sandrock, PB ;

Hou, YQ ;

Xie, SW .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (02) :500-511

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