Ru(II)-Catalyzed C-H Alkenylation of Benzimidates with Unactivated Olefins: A Route to ortho-Alkenylated Benzonitriles

被引：11
|
作者：
Shambhavi, Chikkabagilu Nagaraju [1 ]
Jeganmohan, Masilamani [1 ]
机构：
[1] Indian Inst Technol Madras, Dept Chem, Chennai 600036, Tamil Nadu, India
来源：
ORGANIC LETTERS | 2023年 / 25卷 / 02期
关键词：
OXIDATIVE CYCLIZATION; DIRECTING GROUP; BOND; ALKENES; ACTIVATION; ALKYNES; ARENES; FUNCTIONALIZATION; 1H-INDAZOLES; AROMATICS;
D O I：
10.1021/acs.orglett.2c04036
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A Ru(II)-catalyzed C-H alkenylation of benzimidates with unac-tivated alkenes providing ortho-alkenylated benzonitriles in good to excellent yields in a highly regio-and stereoselective manner is described. In the reaction, an imidate group converted into a nitrile under the reaction conditions. The alkenylation reaction was compatible with various substituted benzimidates as well as functionalized unactivated olefins, including ibuprofen-, neproxen-, coumarin-, and cholesterol-substituted alkenes. A feasible reaction mechanism was proposed to account for the present alkenylation reaction.
引用
收藏
页码：358 / 363
页数：6
相关论文
共 50 条
  • [21] Cobalt-catalyzed chelation assisted C-H allylation of aromatic amides with unactivated olefins
    Yamaguchi, Takuma
    Kommagalla, Yadagiri
    Aihara, Yoshinori
    Chatani, Naoto
    CHEMICAL COMMUNICATIONS, 2016, 52 (66) : 10129 - 10132
  • [22] Rhodium(III)-Catalyzed Aerobic Oxidative C-H Olefination of Unsaturated Acrylamides with Unactivated Olefins
    Logeswaran, Ravichandran
    Jeganmohan, Masilamani
    ORGANIC LETTERS, 2021, 23 (03) : 767 - 771
  • [23] Ru(II)-Catalyzed C-H Activation/Alkylation of 3-Formylbenzofurans with Conjugated Olefins: Product Divergence
    Srinivas, Kolluru
    Siddiqui, Shaziyaparveen K.
    Mudaliar, Jyothi K.
    Ramana, Chepuri V.
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (09): : 5056 - 5066
  • [24] Ni(II)/BINOL-catalyzed alkenylation of unactivated C(sp3)-H bonds
    Liu, Yue-Jin
    Zhang, Zhuo-Zhuo
    Yan, Sheng-Yi
    Liu, Yan-Hua
    Shi, Bing-Feng
    CHEMICAL COMMUNICATIONS, 2015, 51 (37) : 7899 - 7902
  • [25] Ru (II)-Catalyzed C-H Activation: Ketone-Directed Novel 1,4-Addition of Ortho C-H Bond to Maleimides
    Bettadapur, Kiran R.
    Lanke, Veeranjaneyulu
    Prabhu, Kandikere Ramaiah
    ORGANIC LETTERS, 2015, 17 (19) : 4658 - 4661
  • [26] Ruthenium-catalyzed addition of aromatic imines at the ortho C-H bonds to olefins
    Kakiuchi, F
    Yamauchi, M
    Chatani, N
    Murai, S
    CHEMISTRY LETTERS, 1996, (02) : 111 - 112
  • [27] Ruthenium-catalyzed addition of aromatic esters at the ortho C-H bonds to olefins
    Sonoda, M
    Kakiuchi, F
    Kamatani, A
    Chatani, N
    Murai, S
    CHEMISTRY LETTERS, 1996, (02) : 109 - 110
  • [28] Manganese-Catalyzed ortho-Alkenylation of Aromatic Amidines with Alkynes via C-H Activation
    Jia, Teng
    Wang, Congyang
    CHEMCATCHEM, 2019, 11 (21) : 5292 - 5295
  • [29] Ruthenium-catalyzed alkenylation of azoxybenzenes with alkenes through ortho-selective C-H activation
    Li, Hongji
    Xie, Xiaoyu
    Wang, Lei
    CHEMICAL COMMUNICATIONS, 2014, 50 (32) : 4218 - 4221
  • [30] Ruthenium-Catalyzed Ortho-Alkenylation of Aromatic Ketones with Alkenes by C-H Bond Activation
    Padala, Kishor
    Jeganmohan, Masilamani
    ORGANIC LETTERS, 2011, 13 (23) : 6144 - 6147
12345