Formation of new C-O and C-N bonds via base promoted Csp2-Csp3 bond cleavage of α-nitro ketone

被引：15
作者：
Sarma, Manas Jyoti [1 ]
Borah, Arun Jyoti [1 ]
Rajbongshi, Kamal Krishna [1 ]
Phukan, Prodeep [1 ]
机构：
[1] Gauhati Univ, Dept Chem, Gauhati 781014, Assam, India
来源：
TETRAHEDRON LETTERS | 2015年 / 56卷 / 50期
关键词：
C-C cleavage; alpha-Nitroketone; Bromamine-T; Esters; Amide; ACID METHYL-ESTER; ENANTIOSELECTIVE SYNTHESIS; METAL-FREE; ASYMMETRIC AMINOHYDROXYLATION; OXIDATIVE CLEAVAGE; MOLECULAR-OXYGEN; BROMAMINE-T; CARBON; ANTIBACTERIAL; ACTIVATION;
D O I：
10.1016/j.tetlet.2015.11.002
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A catalyst free protocol has been developed for nucleophilic C-sp2 C-sp3 bond cleavage of alpha-nitroketone in the presence of potassium carbonate to create new C-O and C-N bonds. A series of different substituted alpha-nitroketones could be selectively cleaved and converted into corresponding esters and tosylamides in the presence of alcohols and bromamine-T, respectively. (C) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码：7008 / 7011
页数：4
相关论文
共 50 条
  • [1] Formation of esters and amides via metal-free Csp2-Csp3 bond cleavage of α-nitro ketone: Mechanistic insight to the reaction pathway
    Sarma, Manas Jyoti
    Phukan, Prodeep
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2018, 57 (04): : 523 - 533
  • [2] Nickel metallaphotoredox-catalyzed C-O bond activation/Csp2-Csp3 coupling enabled by phosphine
    Fang, Jiaxi
    Jian, Ziheng
    Liu, Huan
    Wang, Yuting
    Yu, Xianbo
    Mou, Zehuai
    Wang, Huifei
    ORGANIC CHEMISTRY FRONTIERS, 2024, 11 (11) : 3058 - 3065
  • [3] Selective Catalytic sp3 C-O Bond Cleavage with C-N Bond Formation in 3-Alkoxy-1-propanols
    Chen, Cheng
    Hong, Soon Hyeok
    ORGANIC LETTERS, 2012, 14 (12) : 2992 - 2995
  • [4] Unexpected C-C bond cleavage of -nitroketone in the presence of TsNBr2: A new pathway for C-N bond formation
    Sarma, Manas Jyoti
    Phukan, Prodeep
    SYNTHETIC COMMUNICATIONS, 2016, 46 (03) : 257 - 262
  • [5] Base-promoted alkylation of P(O)OH compounds with amines via C-N bond cleavage
    Zeng, Kui
    Chen, Lang
    Xiong, Biquan
    Zhou, Yongbo
    Au, Chak-Tong
    Yin, Shuang-Feng
    TETRAHEDRON LETTERS, 2016, 57 (21) : 2222 - 2226
  • [6] Reductive Cleavage of the Csp2-Csp3 Bond of Secondary Benzyl Alcohols: Rhodium Catalysis Directed by N-Containing Groups
    Chen, Kang
    Li, Hu
    Lei, Zhi-Quan
    Li, Yang
    Ye, Wen-He
    Zhang, Li-Sheng
    Sun, Jian
    Shi, Zhang-Jie
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (39) : 9851 - 9855
  • [7] C-O Bond Silylation Catalyzed by Iron: A General Method for the Construction of Csp2-Si Bonds
    Zhang, Juan
    Zhang, Yun
    Geng, Shasha
    Chen, Shuo
    Liu, Zhengli
    Zeng, Xiaoqin
    He, Yun
    Feng, Zhang
    ORGANIC LETTERS, 2020, 22 (07) : 2669 - 2674
  • [8] Benzylic C(sp3)-H Functionalization for C-N and C-O Bond Formation via Visible Light Photoredox Catalysis
    Pandey, Ganesh
    Laha, Ramkrishna
    Singh, Deepak
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (16) : 7161 - 7171
  • [9] Advances in Formation of C-X Bonds via Cleavage of C-N Bond of Quaternary Ammonium Salts
    Wang Yiding
    Li Fuhai
    Zeng Qingle
    ACTA CHIMICA SINICA, 2022, 80 (03) : 386 - 394
  • [10] A Strategy for Accessing Aldehydes via Palladium-Catalyzed C-O/C-N Bond Cleavage in the Presence of Hydrosilanes
    He, Zhanyu
    Wang, Zijia
    Ru, Junxiang
    Wang, Yulin
    Liu, Tingting
    Zeng, Zhuo
    ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (24) : 5794 - 5800
12345