Molecular Iodine-Catalyzed N-Benzylic Sulfonamides C-N Bond Cleavage for the Decarboxylative Substitution of β-Keto Acids

被引：0
|
作者：
Jia, Lina [1 ,2 ]
Zhao, Jinyu [1 ]
Hu, Xiangping [3 ]
机构：
[1] Qiqihar Univ, Coll Chem & Chem Engn, Qiqihar 161006, Peoples R China
[2] Qiqihar Univ, Heilongjiang Prov Key Lab Catalyt Synth Fine Chem, Qiqihar 161006, Peoples R China
[3] Chinese Acad Sci, Dalian Inst Chem Phys, Lab Fine Chem, Dalian 116023, Peoples R China
来源：
LETTERS IN ORGANIC CHEMISTRY | 2022年 / 19卷 / 11期
关键词：
Decarboxylative substitution; iodine; N-benzylic sulfonamide; C-N bond cleavage; beta-keto acids; sp(3); PRIMARY ALLYLIC AMINES; MANNICH REACTION; 1,3-DICARBONYL COMPOUNDS; CARBON-NITROGEN; HALF THIOESTERS; WATER ACCESS; ALKYLATION; KETOACIDS; ALLYLATION; BENZYLATION;
D O I：
10.2174/1570178619666220516124320
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A molecular iodine-catalyzed system for the decarboxylative substitution reactions of beta-keto acids with N-benzylic sulfonamides via sp(3) C-N bond cleavage has been disclosed. This procedure provides a series of alpha-functionalized ketones in good to excellent yields. Furthermore, the practicability of this method could be manifested efficiently in a gram-scale synthesis.
引用
收藏
页码：924 / 930
页数：7
相关论文
共 50 条
  • [21] Iodine-catalyzed oxidative C-C bond cleavage for benzoic acids and benzamides from alkyl aryl ketones
    Sathyanarayana, Pochampalli
    Upare, Atul
    Ravi, Owk
    Muktapuram, Prathap Reddy
    Bathula, Surendar Reddy
    RSC ADVANCES, 2016, 6 (27) : 22749 - 22753
  • [22] Highly Selective and Catalytic C-N Bond Cleavage of Tertiary Sulfonamides: Scope and Mechanistic Insight
    Bhattacharya, Aditya
    Shukla, Pushpendra Mani
    Maji, Biswajit
    ACS OMEGA, 2021, 6 (29): : 18988 - 19005
  • [23] Chelation-assisted decarboxylative C-N bond formation
    Das, Kushal
    Kilaru, Praveen
    Acharya, Sunil
    Zhao, Pinjing
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 257
  • [24] Allylic amination via decarboxylative C-N bond formation
    Mellegaard-Waetzig, SR
    Rayabarapu, DK
    Tunge, JA
    SYNLETT, 2005, (18) : 2759 - 2762
  • [25] Molecular iodine mediated oxidative cleavage of the C-N bond of aryl and heteroaryl (dimethylamino)methyl groups into aldehydes
    Mandrekar, Ketan S.
    Tilve, Santosh G.
    NEW JOURNAL OF CHEMISTRY, 2021, 45 (09) : 4152 - 4155
  • [26] Copper-catalyzed decarboxylative C-N coupling for N-arylation
    Zhang, Yun
    Patel, Sejal
    Mainolfi, Nello
    CHEMICAL SCIENCE, 2012, 3 (11) : 3196 - 3199
  • [27] Iodine-Catalyzed C-N Cleavage of Tertiary Amines: Synthesis of Methylene-Bridged Bis-1,3-dicarbonyl Compounds
    Lu, Lin
    Guo, Shengmei
    Xiong, Qiheng
    Liu, Shengyi
    Li, Xiang
    Cai, Hu
    SYNTHESIS-STUTTGART, 2014, 46 (18): : 2445 - 2450
  • [28] Formal Ring Contraction of Cyclic N-Sulfonamides via C-N Bond Cleavage and α-Amination by Oxidation of Halides
    Nishiguchi, Yuna
    Tomizuka, Akihiko
    Moriyama, Katsuhiko
    ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (23) : 5518 - 5523
  • [29] Caboxylative Coupling of N-(Arylmethyl)sulfonimides with Allyltributylstannane Catalyzed by Palladium Nanoparticles Involving Benzylic C-N Cleavage
    Wu, Chaolin
    Xie, Yanlong
    Song, Jiliang
    Feng, Xiujuan
    Jian, Siqi
    Lu, Wenchao
    Zhu, Jiuzhen
    Yamamoto, Yoshinori
    Bao, Ming
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2025, 14 (01)
  • [30] Nickel-catalyzed C-N bond reduction of aromatic and benzylic quaternary ammonium triflates
    Yi, Yuan-Qiu-Qiang
    Yang, Wen-Cheng
    Zhai, Dan-Dan
    Zhang, Xiang-Yu
    Li, Shuai-Qi
    Guan, Bing-Tao
    CHEMICAL COMMUNICATIONS, 2016, 52 (72) : 10894 - 10897
12345