A reductive Sandmeyer-type reaction for the synthesis of sulfoxides from anilines under photocatalysis

被引:8
|
作者
Peng, Gangqi [1 ]
Cheng, Hao [1 ]
Cheng, Xiya [1 ]
He, Yang [1 ]
An, Yuanyuan [1 ]
Wu, Jie [2 ,3 ]
Zheng, Danqing [1 ]
机构
[1] Nanjing Tech Univ, Coll Chem Engn, State Key Lab Mat Oriented Chem Engn, South Puzhu Rd 30, Nanjing 210009, Peoples R China
[2] Taizhou Univ, Inst Adv Studies, Sch Pharmaceut & Chem Engn, 1139 Shifu Ave, Taizhou 318000, Peoples R China
[3] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China
关键词
PALLADIUM-CATALYZED ARYLATION; DIAZONIUM SALTS; DIARYL SULFOXIDES; ARYLBORONIC ACIDS; SULFUR-DIOXIDE; CHEMISTRY; EFFICIENT; LIGANDS; CYANATION;
D O I
10.1039/d3qo00297g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A reductive Sandmeyer-type sulfinylation reaction of aryldiazonium salts with sodium sulfinates is reported. The reaction takes place under photocatalysis, generating a range of valuable sulfoxides via a radical substitution pathway. Aromatic amines can also be converted to the corresponding sulfoxides via in situ diazotization in a one-pot, two-step process. The late-stage sulfinylation of drug-based amines further demonstrated the practicality of this method.
引用
收藏
页码:3033 / 3038
页数:6
相关论文
共 50 条
  • [1] Sandmeyer-Type Reductive Disulfuration of Anilines
    Chen, Shiqi
    Cao, Si
    Liu, Chaoyang
    Wang, Baoxu
    Ren, Xiaorui
    Huang, Hang
    Peng, Zhihong
    Wang, Xi
    ORGANIC LETTERS, 2021, 23 (19) : 7428 - 7433
  • [2] Synthesis of Aryl Trimethylstannanes from Aryl Amines: A Sandmeyer-Type Stannylation Reaction
    Qiu, Di
    Meng, He
    Jin, Liang
    Wang, Shuai
    Tang, Shengbo
    Wang, Xi
    Mo, Fanyang
    Zhang, Yan
    Wang, Jianbo
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (44) : 11581 - 11584
  • [3] Copper-free Sandmeyer-type Reaction for the Synthesis of Sulfonyl Fluorides
    Zhong, Tao
    Pang, Meng-Ke
    Chen, Zhi-Da
    Zhang, Bin
    Weng, Jiang
    Lu, Gui
    ORGANIC LETTERS, 2020, 22 (08) : 3072 - 3078
  • [4] Zn-promoted Sandmeyer-type reductive chalcogenation of (hetero)aryl diazonium salts
    Fan, Qiujin
    Zhao, Yanchuang
    Wang, Junhong
    Bai, Ying
    Zhou, Shengbin
    Shao, Xinxin
    ORGANIC CHEMISTRY FRONTIERS, 2025,
  • [5] Copper-Promoted One-Pot Sandmeyer-Type Reaction for the Synthesis of N-Aryltriazoles
    Cui, Menghan
    Wang, Rong
    Yang, Qing
    Kuang, Chunxiang
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (15): : 9654 - 9662
  • [6] Sandmeyer-Type Reaction to Pinacol Arylboronates in Water Phase: A Green Borylation Process
    Zhang, Jie
    Wang, Xiaolong
    Yu, Haitao
    Ye, Jiahai
    SYNLETT, 2012, (09) : 1394 - 1396
  • [7] Metal-Free Aromatic Carbon-Phosphorus Bond Formation via a Sandmeyer-Type Reaction
    Wang, Shuai
    Qiu, Di
    Mo, Fanyang
    Zhang, Yan
    Wang, Jianbo
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (23): : 11603 - 11611
  • [8] Arenesulfonyl Fluoride Synthesis via Copper-free Sandmeyer-type Fluorosulfonylation of Arenediazonium Salts
    Lin, Qiongzhen
    Ma, Zhanhu
    Zheng, Changge
    Hu, Xiao-Jun
    Guo, Yong
    Chen, Qing-Yun
    Liu, Chao
    CHINESE JOURNAL OF CHEMISTRY, 2020, 38 (10) : 1107 - 1110
  • [9] Diazotization-bromination of aromatic amines using polymer-supported bromide via Sandmeyer-type reaction
    Mohammad Ali Karimi Zarchi
    S. Zahra Mousavi
    Journal of Polymer Research, 2014, 21
  • [10] Diazotization-bromination of aromatic amines using polymer-supported bromide via Sandmeyer-type reaction
    Zarchi, Mohammad Ali Karimi
    Mousavi, S. Zahra
    JOURNAL OF POLYMER RESEARCH, 2013, 21 (01)