Metal-Free Aerobic Oxidative Cyanation of Tertiary Amines: Azobis(isobutyronitrile) (AIBN) as a Sole Cyanide Source

被引:27
|
作者
Liu, Peng-Yu [1 ]
Zhang, Chao [1 ]
Zhao, Shi-Chen [1 ]
Yu, Fang [1 ]
Li, Fei [1 ]
He, Yu-Peng [1 ]
机构
[1] Liaoning Shihua Univ, Coll Chem Chem Engn & Environm Engn, Dandong Lu West 1, Fushun 113001, Peoples R China
来源
JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 82卷 / 23期
基金
中国国家自然科学基金;
关键词
COPPER-CATALYZED CYANATION; H BOND ACTIVATION; ALPHA-CYANATION; STRECKER REACTION; SODIUM-CYANIDE; COUPLING REACTIONS; HYDROGEN-PEROXIDE; HIGHLY EFFICIENT; NITRILES; AZOBISISOBUTYRONITRILE;
D O I
10.1021/acs.joc.7b02021
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An aerobic oxidative cyanation for the synthesis of alpha-aminonitriles was reported. The formation of C(sp(3))-CN bonds was achieved under a metal-free condition by utilizing azobis(isobutyronitrile) as a sole organic cyanide source with the combination of pivalic acid and sodium acetate as additives.
引用
收藏
页码:12786 / 12790
页数:5
相关论文
共 50 条
  • [21] Cobalt-Catalyzed Oxidative α-Cyanation of Tertiary Aromatic Amines with Trimethylsilyl Cyanide and tert-Butyl Hydroperoxide
    Sakai, Norio
    Mutsuro, Akihiro
    Ikeda, Reiko
    Konakahara, Takeo
    [J]. SYNLETT, 2013, 24 (10) : 1283 - 1285
  • [22] Sulfuryl Chloride as an Efficient Initiator for the Metal-Free Aerobic Cross-Dehydrogenative Coupling Reaction of Tertiary Amines
    Tanoue, Arata
    Yoo, Woo-Jin
    Kobayashi, Shu
    [J]. ORGANIC LETTERS, 2014, 16 (09) : 2346 - 2349
  • [23] Direct oxidative phosphonylation of amines under metal-free conditions
    Wang, Haolong
    Li, Xincheng
    Wu, Fan
    Wan, Boshun
    [J]. TETRAHEDRON LETTERS, 2012, 53 (06) : 681 - 683
  • [24] A Metal-Free Oxidative Amination of Benzoxazoles with Primary Amines and Ammonia
    Kloeckner, Ulrich
    Weckenmann, Nicole M.
    Nachtsheim, Boris J.
    [J]. SYNLETT, 2012, 23 (01) : 97 - 100
  • [25] Hydrothermal Carbonization of Renewable Natural Plants as Superior Metal-Free Catalysts for Aerobic Oxidative Coupling of Amines to Imines
    Liu, Chan
    Li, Na
    Peng, Ling
    Zhong, Wenzhou
    Mao, Liqiu
    Yin, Dulin
    [J]. ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2020, 8 (30): : 11404 - 11412
  • [26] Metal-free reductive amination of aldehydes for the synthesis of secondary and tertiary amines
    Ambica
    Khajuria, Rajni
    Saini, Yeshwinder
    Kapoor, Kamal K.
    [J]. INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2015, 54 (10): : 1252 - 1259
  • [27] Efficient metal-free hydrositylation of tertiary, secondary and primary amides to amines
    Blondiaux, Enguerrand
    Cantat, Thibault
    [J]. CHEMICAL COMMUNICATIONS, 2014, 50 (66) : 9349 - 9352
  • [28] Metal-Free Conversion of Carboxamides to Ureas Using Tertiary Amines and Iodosylmesitylene
    Han, Hoon
    Chang, Sukbok
    [J]. BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2010, 31 (03): : 746 - 748
  • [29] AIBN-Initiated Oxidative Deoximation Reaction: A Metal-Free and Environmentally-Friendly Protocol
    Wang, Feng
    Chen, Tian
    Shi, Yaocheng
    Yu, Lei
    [J]. ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 10 (03) : 614 - 618
  • [30] Mechanisms of Metal-Free Aerobic Oxidation To Prepare Benzoxazole Catalyzed by Cyanide: A Direct Cyclization or Stepwise Oxidative Dehydrogenation and Cyclization?
    Chen, Weiqiang
    An, Weili
    Wang, Yongjian
    Yu, Ao
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (22): : 10857 - 10862