Oxidative C(sp2)-H Phosphonation of Aldehyde Hydrazones

被引：67
|
作者：
Xu, Pan [1 ]
Wu, Zhongkai [1 ]
Zhou, Nengneng [1 ]
Zhu, Chengjian [1 ,2 ]
机构：
[1] Nanjing Univ, Sch Chem & Chem Engn, State Key Lab Coordinat Chem, Nanjing 210093, Jiangsu, Peoples R China
[2] Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
来源：
ORGANIC LETTERS | 2016年 / 18卷 / 05期
基金：
中国国家自然科学基金;
关键词：
C-H BONDS; ELECTROPHILIC SUBSTITUTION; ALPHA-AMINOPHOSPHONATES; PHOSPHORYLATION; N; N-DIALKYLHYDRAZONES; FUNCTIONALIZATION; DIFLUOROALKYLATION; HYDROGENATION; INHIBITORS; LIGANDS;
D O I：
10.1021/acs.orglett.6b00257
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A K2S2O8/Cu(OAc)(2)-mediated oxidative C-H/P-H cross coupling of aldehyde hydrazones with diphenylphosphine oxide for the direct preparation of functionalized alpha-iminophosphine oxides is reported. The reaction shows good functional group tolerance and proceeds smoothly under mild conditions. This strategic protocol for C-P bond formation is facilitated by a net oxidative aminyl radical polar crossover process.
引用
收藏
页码：1143 / 1145
页数：3
相关论文
共 50 条
  • [21] Copper-Catalyzed Intramolecular C(sp3)-H and C(sp2)-H Amidation by Oxidative Cyclization
    Wang, Zhen
    Ni, Jizhi
    Kuninobu, Yoichiro
    Kanai, Motomu
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (13) : 3496 - 3499
  • [22] C-H Trifluoromethylthiolation of aldehyde hydrazones
    Levet, Victor
    Ramesh, Balu
    Wang, Congyang
    Besset, Tatiana
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2024, 20 : 2883 - 2890
  • [23] Organocatalytic Oxidative C-H Amination of Aldehyde Hydrazones with Azoles at Ambient Temperature
    Ghosh, Asim Kumar
    Neogi, Sukanya
    Das, Krishna Kanta
    Hajra, Alakananda
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (09): : 5682 - 5689
  • [24] Silver in C(sp2)-H Functionalization
    Liu, Feng
    Zhang, Zhen
    Diao, Hai-yan
    Shi, Zhang-jie
    CHEMCATCHEM, 2021, 13 (06) : 1475 - 1497
  • [25] Metal-free oxidative tandem coupling of activated alkenes with carbonyl C(sp2)-H bonds and aryl C(sp2)-H bonds using TBHP
    Zhou, Ming-Bo
    Song, Ren-Jie
    Ouyang, Xuan-Hui
    Liu, Yu
    Wei, Wen-Ting
    Deng, Guo-Bo
    Li, Jin-Heng
    CHEMICAL SCIENCE, 2013, 4 (06) : 2690 - 2694
  • [26] Asymmetric C(sp2)-H Activation
    Wencel-Delord, Joanna
    Colobert, Francoise
    CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (42) : 14010 - 14017
  • [27] Electrochemical oxidative Z-selective C(sp2)-H chlorination of acrylamides
    Harnedy, James
    Hareram, Mishra Deepak
    Tizzard, Graham J.
    Coles, Simon J.
    Morrill, Louis C.
    CHEMICAL COMMUNICATIONS, 2021, 57 (94) : 12643 - 12646
  • [28] Room temperature C(sp2)-H oxidative chlorination via photoredox catalysis
    Zhang, Lei
    Hu, Xile
    CHEMICAL SCIENCE, 2017, 8 (10) : 7009 - 7013
  • [29] Oxidative C(sp2)-H trifluoromethylation of enamides using TMSCF3
    Munoz, Socrates
    Krishnamurti, Vinayak
    Prakash, G. K.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 254
  • [30] Iron catalyzed oxidative SP2 C-H activation in the synthesis of phenanthridinones
    Chen, Shuai
    Reitz, Allen
    Garry, Smith
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 252
12345