Rh(III)-Catalyzed Tandem Oxidative Olefination-Michael Reactions between Aryl Carboxamides and Alkenes

被引：264
|
作者：
Wang, Fen [1 ]
Song, Guoyong [1 ]
Li, Xingwei [1 ]
机构：
[1] Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Peoples R China
来源：
ORGANIC LETTERS | 2010年 / 12卷 / 23期
关键词：
C-H BOND; INTERNAL ALKYNES; ROOM-TEMPERATURE; BENZOIC-ACIDS; ACTIVATION; FUNCTIONALIZATION; ARYLATION; INDOLES; COUPLING/CYCLIZATION; ALKYLATION;
D O I：
10.1021/ol102241f
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Rh(III)-catalyzed oxidative coupling reactions between benzamides or heteroaryl carboxamides and olefins have been developed. The vinylation product can further undergo a Michael reaction leading to gamma-lactam in the case of electron-withdrawing olefins.
引用
收藏
页码：5430 / 5433
页数：4
相关论文
共 50 条
  • [21] Synthesis of π-Extended Heterocycles via Rh(III)-Catalyzed Oxidative Annulation of 5-Aryl Pyrazinones with Alkynes
    Oh, Harin
    Byun, Hee Won
    Moon, Kyeongwon
    Kim, Saegun
    Ghosh, Prithwish
    An, Won
    Kwak, Jong Hwan
    Park, Jung Su
    Mishra, Neeraj Kumar
    Kim, In Su
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (23): : 16349 - 16360
  • [22] Aerobic Oxidative C-H Olefination of Arylamides with Unactivated Olefins via a Rh(III)-Catalyzed C-H Activation
    Jambu, Subramanian
    Shambhavi, Chikkabagilu Nagaraju
    Jeganmohan, Masilamani
    ORGANIC LETTERS, 2021, 23 (08) : 2964 - 2970
  • [23] Rh(III)-Catalyzed Tandem C-H Allylation and Oxidative Cyclization of Anilides: A New Entry to Indoles
    Cajaraville, Ana
    Lopez, Susana
    Varela, Jesus A.
    Saa, Carlos
    ORGANIC LETTERS, 2013, 15 (17) : 4576 - 4579
  • [24] Oxidative Olefination of Anilides with Unactivated Alkenes Catalyzed by an (Electron-Deficient 5-Cyclopentadienyl)Rhodium(III) Complex Under Ambient Conditions
    Takahama, Yuji
    Shibata, Yu
    Tanaka, Ken
    CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (25) : 9053 - 9056
  • [25] Synthesis of Cinnolines and Cinnolinium Salt Derivatives by Rh(III)-Catalyzed Cascade Oxidative Coupling/Cyclization Reactions
    Wang, Yanwei
    Li, Bin
    Wang, Baiquan
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (18): : 10845 - 10854
  • [26] Tandem Rh(III)-Catalyzed C-H Amination/Annulation Reactions: Synthesis of Indoloquinoline Derivatives in Water
    Shi, Liangliang
    Wang, Baiquan
    ORGANIC LETTERS, 2016, 18 (12) : 2820 - 2823
  • [27] Rh(III)-catalyzed oxidative coupling of unactivated alkenes via C-H activation: Reaction development and mechanistic insights
    Tsai, Andy S.
    Brasse, Mikael
    Ellman, Jonathan A.
    Bergman, Robert G.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 243
  • [28] Rhodium(III)-Catalyzed Tandem C-H Olefination and Oxidative Cyclization of Aromatic Acids with Acrylates for the Synthesis of (E)-3-Ylidenephthalides
    Han, Wen-Jing
    Pu, Fan
    Fan, Juan
    Liu, Zhong-Wen
    Shi, Xian-Ying
    ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (20) : 3520 - 3525
  • [29] From Indoles to Carbazoles: Tandem Cp*Rh(III)-Catalyzed C-H Activation/Bronsted Acid-Catalyzed Cyclization Reactions
    Wu, Jia-Qiang
    Yang, Zhen
    Zhang, Shang-Shi
    Jiang, Chun-Yong
    Li, Qingjiang
    Huang, Zhi-Shu
    Wang, Honggen
    ACS CATALYSIS, 2015, 5 (11): : 6453 - 6457
  • [30] Aerobic Oxidative Alkenylation of Weak O-Coordinating Arylacetamides with Alkenes via a Rh(III)-Catalyzed C-H Activation
    Jambu, Subramanian
    Sivasakthikumaran, Ramakrishnan
    Jeganmohan, Masilamani
    ORGANIC LETTERS, 2019, 21 (05) : 1320 - 1324
12345