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
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
  • [31] CLEAVAGE OF C-N BOND IN N,N'-BIS "[DI(VINYLOXYETHYL)]METHYLENEDIAMINE
    ATAVIN, AS
    DMITRIEV.ZT
    ZHURNAL ORGANICHESKOI KHIMII, 1972, 8 (03): : 472 - &
  • [32] A vanadium-promoted C-N bond cleavage
    Egdal, RK
    Larsen, FB
    Bond, AD
    McKenzie, CJ
    INORGANICA CHIMICA ACTA, 2005, 358 (02) : 376 - 382
  • [33] Unique copper ion catalyzed hydrolytic cleavage of C-N(2) bond of thiosemicarbazide
    Chawla, SK
    Arora, M
    Nättinen, K
    Rissanen, K
    POLYHEDRON, 2006, 25 (03) : 627 - 634
  • [34] Stille Coupling via C-N Bond Cleavage
    Zanda, Matteo
    SYNTHESIS-STUTTGART, 2017, 49 (03): : A20 - A21
  • [35] Stille coupling via C-N bond cleavage
    Wang, Dong-Yu
    Kawahata, Masatoshi
    Yang, Ze-Kun
    Miyamoto, Kazunori
    Komagawa, Shinsuke
    Yamaguchi, Kentaro
    Wang, Chao
    Uchiyama, Masanobu
    NATURE COMMUNICATIONS, 2016, 7
  • [36] A Convenient Method for Cleavage of Amide C-N Bond
    Wei, Yingfei
    Shi, Daxing
    Wei, Zhen
    Xu, Juan
    Li, Jiarong
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2012, 32 (06) : 1126 - 1130
  • [37] Vinylation of Benzylic Amines via C-N Bond Functionalization of Benzylic Pyridinium Salts
    Guan, Weiye
    Liao, Jennie
    Watson, Mary P.
    SYNTHESIS-STUTTGART, 2018, 50 (16): : 3231 - 3237
  • [38] Vinylation of benzylic amines via C-N bond functionalization of benzylic pyridinium salts
    Guan, Weiye
    Liao, Jennie
    Watson, Mary
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 258
  • [39] Visible-Light-Triggered C-C and C-N Bond Formation by C-S Bond Cleavage of Benzylic Thioethers
    Lanzi, Matteo
    Merad, Jeremy
    Boyarskaya, Dina V.
    Maestri, Giovanni
    Allain, Clemence
    Masson, Geraldine
    ORGANIC LETTERS, 2018, 20 (17) : 5247 - 5250
  • [40] Catalyst-Free Alkylation of Sulfinic Acids with Sulfonamides via Sp3 C-N Bond Cleavage at Room Temperature
    Liu, Cong-Rong
    Li, Man-Bo
    Cheng, Dao-Juan
    Yang, Cui-Feng
    Tian, Shi-Kai
    ORGANIC LETTERS, 2009, 11 (12) : 2543 - 2545