Copper-catalyzed denitrogenative N-arylation of sulfoximines and sulfonamides with arylhydrazines

被引：13
|
作者：
Dong, Wanrong [1 ]
Liu, Chaoyang [1 ]
Ma, Xinchi [1 ]
Zhang, Yingjun [2 ]
Peng, Zhihong [1 ]
Xie, Dexun [3 ]
An, Delie [1 ]
机构：
[1] Hunan Univ, Coll Chem & Chem Engn, State Key Lab Chemo Biosensing & Chemometr, Changsha 410082, Hunan, Peoples R China
[2] Sunshine Lake Pharma Co Ltd, State Key Lab Antiinfect Drug Dev 2015DQ780357, Dongguan 523871, Peoples R China
[3] Aneo Chem Tech Co Ltd, Guangzhou 510670, Guangdong, Peoples R China
来源：
TETRAHEDRON | 2019年 / 75卷 / 29期
关键词：
Copper catalysis; Dehydrogenative arylation; Arylhydrazines; NH-Sulfoximines; Sulfonamides; ARYL BROMIDES; ARYLBORONIC ACIDS; REUSABLE CATALYST; COUPLING REACTION; BOND FORMATION; BORONIC ACIDS; LIGAND-FREE; PALLADIUM; IODIDES; EFFICIENT;
D O I：
10.1016/j.tet.2019.05.039
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A Cu-mediated ligand-free arylation of NH-sulfoximines and sulfonamides by aryihydrazine hydrochlorides was herein demonstrated. The oxidative transformation provided an easy access towards N-aryl sulfoximines and sulfonamides in high yields (up to 93% yields) with broad functional groups tolerance (up to 36 examples). The protocol was proposed to take place through the free radical pathway based on the results of control reactions and EPR analysis. (C) 2019 Elsevier Ltd. All rights reserved.
引用
收藏
页码：3886 / 3893
页数：8
相关论文
共 50 条
  • [1] Palladium-Catalyzed Denitrogenative Arylation of Sulfoximines and Sulfonamides with Arylhydrazines under Mild Conditions
    Peng, Ruyi
    Zhao, Zijian
    Zhao, Yongxin
    Luo, Zhenghong
    Lian, Yan
    [J]. INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2021, 31 (03) : 333 - 340
  • [2] Ligand-free copper-catalyzed denitrogenative arylation of phosphorylamides with arylhydrazines
    Zhu, Qiao
    Che, Shiying
    Luo, Zhenghong
    Zhao, Zijian
    [J]. SYNTHETIC COMMUNICATIONS, 2020, 50 (07) : 947 - 957
  • [3] Efficient Ligand-Free, Copper-Catalyzed N-Arylation of Sulfonamides
    Teo, Yong-Chua
    Yong, Fui-Fong
    [J]. SYNLETT, 2011, (06) : 837 - 843
  • [4] Copper-Catalyzed N-Arylation of Sulfoximines with Arylboronic Acids under Mild Conditions
    Gupta, Surabhi
    Baranwal, Siddharth
    Muniyappan, Nalluchamy
    Sabiah, Shahulhameed
    Kandasamy, Jeyakumar
    [J]. SYNTHESIS-STUTTGART, 2019, 51 (10): : 2171 - 2182
  • [5] Efficient copper-catalyzed N-arylation of sulfoximines with aryl iodides and aryl bromides
    Sedelmeier, J
    Bolm, C
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (17): : 6904 - 6906
  • [6] The copper-catalyzed N-arylation of indoles
    Antilla, JC
    Klapars, A
    Buchwald, SL
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (39) : 11684 - 11688
  • [7] Copper-Catalyzed N-Arylation of Sulfonimidamides
    Azzaro, Stephane
    Desage-El Murr, Marine
    Fensterbank, Louis
    Lacote, Emmanuel
    Malacria, Max
    [J]. SYNLETT, 2011, (06) : 849 - 851
  • [8] Copper-catalyzed N-arylation of oxindoles
    Phillips, Dean P.
    Hudson, Andrew R.
    Nguyen, Bao
    Lau, Thomas L.
    McNeill, Matthew H.
    Dalgard, Jackline E.
    Chen, Jyun-Hung
    Penuliar, Richard J.
    Miller, Todd A.
    Zhi, Lin
    [J]. TETRAHEDRON LETTERS, 2006, 47 (40) : 7137 - 7138
  • [9] Copper-catalyzed N-arylation of Indoles
    Hisana, Kalathingal Nasreen
    Abdulla, Cheriya Mukkolakkol Afsina
    Anilkumar, Gopinathan
    [J]. CURRENT ORGANIC CHEMISTRY, 2022, 26 (09) : 857 - 886
  • [10] Copper-Catalyzed Ultrasound-Expedited N-Arylation of Sulfoximines using Diaryliodonium Salts
    Vaddula, Buchireddy
    Leazer, John
    Varma, Rajender S.
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (06) : 986 - 990
12345