Simple and efficient copper-catalyzed S-arylation of diaryl disulfides with triarylbismuthanes under aerobic conditions

被引：29
|
作者：
Yasuike, Shuji [1 ,2 ]
Nishioka, Motokazu [1 ]
Kakusawa, Naoki [1 ]
Kurita, Jyoji [1 ]
机构：
[1] Hokuriku Univ, Fac Pharmaceut Sci, Kanazawa, Ishikawa 9201181, Japan
[2] Hokuriku Univ, Org Frontier Res Prevent Pharmaceut Sci, Kanazawa, Ishikawa 9201181, Japan
来源：
TETRAHEDRON LETTERS | 2011年 / 52卷 / 48期
关键词：
Cross-coupling; S-Arylation; Bismuthane; Disulfide; Copper catalyst; CROSS-COUPLING REACTIONS; C-S; ARYL IODIDES; N-ARYLATION; BOND FORMATION; ORGANOBORONIC ACIDS; O-PHENYLATION; BORONIC ACIDS; TE BOND; LIGAND;
D O I：
10.1016/j.tetlet.2011.09.071
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Novel and simple copper-catalyzed C(aryl)-S bond formation of diaryl disulfides with bismuth reagents is described. Reactions of diaryl disulfides with triarylbismuthanes in the presence of CuOAc (10 mol %) and 1,10-phenanthroline (10 mol %) under aerobic conditions led to the formation of unsymmetrical diaryl sulfides in satisfactory yields. The reaction is atom-economic and all three aryl groups of the triarylbismuthanes and both sulfanyl groups of the diaryl disulfides could be transferred to the coupling products. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码：6403 / 6406
页数：4
相关论文
共 50 条
  • [1] Simple and efficient copper-catalyzed synthesis of symmetrical diaryl selenides from triarylbismuthanes and selenium under aerobic conditions
    Matsumura, Mio
    Kumagai, Hanae
    Murata, Yuki
    Kakusawa, Naoki
    Yasuike, Shuji
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2016, 807 : 11 - 16
  • [2] Copper-Catalyzed S-Arylation of Tetraalkylthiuram Disulfides by Using Diaryliodonium Salts
    Zeng, Meng-Tian
    Xu, Wan
    Liu, Xing
    Chang, Cai-Zhu
    Zhu, Hui
    Dong, Zhi-Bing
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (40) : 6060 - 6066
  • [3] Synthesis of Unsymmetrical Diaryl Selenides: Copper-Catalyzed Se-Arylation of Diaryl Diselenides with Triarylbismuthanes
    Matsumura, Mio
    Shibata, Kohki
    Ozeki, Sota
    Yamada, Mizuki
    Murata, Yuki
    Kakusawa, Naoki
    Yasuike, Shuji
    SYNTHESIS-STUTTGART, 2016, 48 (05): : 730 - 736
  • [4] Efficient Copper-Catalyzed S-Arylation of Thiols with Aryl Bromides and Chlorides
    Li, Yaming
    Li, Xiaoying
    Wang, Huifeng
    Chen, Tao
    Xie, Yusheng
    SYNTHESIS-STUTTGART, 2010, (21): : 3602 - 3608
  • [5] Copper-Catalyzed S-Arylation of Arylthioureas by Using Diaryliodonium Salts
    Zhu, Hui
    Liu, Xing
    Cheng, Yu
    Peng, Han-Ying
    Li, Yue-Sheng
    Dong, Zhi-Bing
    SYNTHESIS-STUTTGART, 2018, 50 (11): : 2247 - 2254
  • [6] Copper-catalyzed S-arylation of tetramethylguanidine-heterocumulene adducts
    Yavari, Issa
    Nematpour, Manijeh
    Damghani, Tahereh
    TETRAHEDRON LETTERS, 2014, 55 (07) : 1323 - 1325
  • [7] Single-atom copper catalyst for the S-arylation reaction to produce diaryl disulfides
    Zhao Y.
    Zhou Y.
    Lv S.
    Li H.
    Wu Q.
    Liu S.
    Li W.
    Chen T.
    Chen Z.
    Chemical Science, 2023, 14 (17) : 4620 - 4626
  • [8] Synthesis of Sulfilimines Enabled by Copper-Catalyzed S-Arylation of Sulfenamides
    Liang, Qingjin
    Wells, Lucille A.
    Han, Kaiming
    Chen, Shufeng
    Kozlowski, Marisa C.
    Jia, Tiezheng
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2023, 145 (11) : 6310 - 6318
  • [9] An efficient iron-catalyzed S-arylation of aryl and alkylthiols with aryl halides in the presence of water under aerobic conditions
    Sindhu, K. S.
    Thankachan, Amrutha P.
    Thomas, Anns Maria
    Anilkumar, Gopinathan
    TETRAHEDRON LETTERS, 2015, 56 (34) : 4923 - 4926
  • [10] EFFICIENT COPPER-CATALYZED DOUBLE S-ARYLATION OF ARYL HALIDES WITH SODIUM SULFIDE IN PEG-400
    Chen, Junmin
    Zhang, Yimin
    Liu, Li
    Yuan, Tangjun
    Yi, Fei
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2012, 187 (11) : 1284 - 1290
12345