I2-Mediated Site-Selective C-H Functionalization: Access to p-Amino-Substituted Unsymmetrical Benzils and Quinoxalines from Sulfoxonium Ylides

被引:3
|
作者
Saini, Rahul Kumar [1 ]
Borpatra, Paran J. [1 ]
Chaubey, Trayambek Nath [1 ]
Pandey, Satyendra Kumar [1 ]
机构
[1] Banaras Hindu Univ, Inst Sci, Dept Chem, Varanasi 221005, Uttar Pradesh, India
来源
JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 08期
关键词
ONE-POT SYNTHESIS; METHYL KETONES; CATALYZED OXIDATION; EFFICIENT SYNTHESIS; ORTHO-HALOGENATION; ALPHA-KETOAMIDES; IN-VITRO; ANILINES; DERIVATIVES; ALKYNES;
D O I
10.1021/acs.joc.3c02975
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An I2-mediated approach for selective C-H functionalization of unprotected aniline derivatives for synthesizing benzils and quinoxaline derivatives from sulfoxonium ylides has been described. Aniline derivatives and sulfoxonium ylides ornamented with different functional groups showed good compatibility. They afforded the corresponding products with moderate to high yields via a mild and simple procedure. Finally, we validated the practicality of this method by scaling up the reaction and further conversion of the synthesized derivatives into other valuable molecules.
引用
收藏
页码:5536 / 5545
页数:10
相关论文
共 34 条
  • [21] PhI(OAc)2-Promoted Site-Selective C-H Chlorination of (Hetero)arenes with p-Toluenesulfonyl Chloride
    Tang, Junyang
    Liu, Yaorong
    Qiu, Baojie
    Zhang, Zhuo
    Zhang, Xingxian
    ORGANIC LETTERS, 2024, 26 (41) : 8708 - 8712
  • [22] Expanding the Utility of Inexpensive Pyridine-N-oxide Directing Group for the Site-selective sp2/sp3 γ-C-H and sp2 δ-C-H Functionalization of Carboxamides
    Tomar, Radha
    Kumar, Amit
    Dalal, Arup
    Bhattacharya, Debabrata
    Singh, Prabhakar
    Babu, Srinivasarao Arulananda
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 11 (09)
  • [23] Manganese(I)-Catalyzed Site-Selective C6-Alkenylation of 2-Pyridones Using Alkynes via C-H Activation
    Wan, Shanhong
    Luo, Zhenli
    Xu, Xin
    Yu, Haiyang
    Li, Jiajie
    Pan, Yixiao
    Zhang, Xin
    Xu, Lijin
    Cao, Rui
    ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (10) : 2586 - 2593
  • [24] CuI/I2-Mediated Intramolecular Oxidative Cyclization Reaction of N-(2-pyridyl)amidines by the Direct Double C-H Functionalization of a C(sp3)-H Bond
    Yi, Fengping
    Zhang, Songxing
    Zhang, Lirong
    Yi, Weiyin
    Yu, Rui
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 6 (12) : 1808 - 1817
  • [25] Site-Selective Functionalization of Unactivated Allylic C-H Bonds via Direct Deprotonation with KTMP: Application to the Formal Total Synthesis of (+)-Artemisinin from Amorphadiene
    Clanton, Nicholas A.
    Wilson, Nicolas A.
    Ortiz, Eliezer
    Blumberg, Shawn T.
    Frantz, Doug E.
    ORGANIC LETTERS, 2023, 25 (01) : 277 - 281
  • [26] Maleimide-Dependent Rh(III)-Catalyzed Site-Selective Mono and Dual C-H Functionalization of 2-Arylbenzo[d]thiazole and Oxazole Derivatives
    Kumari, Vidya
    Acharya, Swadhin Swaraj
    Mondal, Nurabul
    Choudhury, Lokman H.
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (24): : 18003 - 18018
  • [27] Ag(I)-Mediated Site-Selective C(sp2)-H Chalcogenation of Tryptophan-Peptides with Dichalcogenides at Room Temperature
    Bag, Raghunath
    Kar, Malobika
    Sharma, Nagendra K.
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (20): : 14981 - 15002
  • [28] Iron(III) Chloride Mediated para-Selective C-H Functionalization: Access to C5-Chloro and C5,C7-Dichloro/Dianisyl Substituted 2-Arylbenzoxazoles
    Sahoo, Kanchanbala
    Panda, Niranjan
    ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (05) : 1023 - 1030
  • [29] Silver-mediated C-H bond functionalization: one-pot to construct substituted indolizines from 2-alkylazaarenes with alkynes
    Tan, Xian-chun
    Liang, Ying
    Bao, Fang-ping
    Wang, Heng-shan
    Pan, Ying-ming
    TETRAHEDRON, 2014, 70 (38) : 6717 - 6722
  • [30] Photoinduced Site-Selective Aryl C-H Borylation with Electron-Donor-Acceptor Complex Derived from B2Pin2 and Isoquinoline
    Li, Manhong
    Deng, Yi-Hui
    Chang, Qianqian
    Li, Jinyuan
    Wang, Chao
    Wang, Leifeng
    Sun, Tian-Yu
    MOLECULES, 2024, 29 (08):