Pd(II)-catalyzed, controllable C-H mono-/diarylation of aryl tetrazoles: concise synthesis of Losartan

被引:11
|
作者
Ding, Yan-Jun [1 ]
Li, Yan [1 ]
Dai, Sheng-Yu [1 ]
Lan, Quan [1 ]
Wang, Xi-Sheng [1 ]
机构
[1] Univ Sci & Technol China, Dept Chem, Hefei 230026, Anhui, Peoples R China
基金
中国博士后科学基金;
关键词
EFFICIENT CATALYTIC-SYSTEM; CROSS-COUPLING REACTIONS; ORTHO-ARYLATION; ANGIOTENSIN-II; DIRECTING GROUP; BOND FUNCTIONALIZATION; NATURAL-PRODUCTS; PALLADIUM; ACTIVATION; BROMIDES;
D O I
10.1039/c4ob02453b
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A palladium(II)-catalyzed C-H arylation directed by tetrazole, a metabolically stable surrogate for the carboxylic acid group in drug design, has been developed. Excellent mono-/di-selectivity was achieved through adjustment of the protecting site on the tetrazole ring. The synthetic utility of this new transformation was demonstrated in the concise total synthesis of Losartan.
引用
收藏
页码:3198 / 3201
页数:4
相关论文
共 50 条
  • [21] Computational exploration of Pd(II)-catalyzed C-H activations
    Bay, Katherine
    Houk, Kendall
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 256
  • [22] Ligand-Dependant Selective Synthesis of Mono- and Dialkenylcarbazoles through Rhodium(III)-Catalyzed C-H Alkenylation
    Tanaka, Rikuto
    Ochiai, Shiho
    Sakai, Asumi
    Usuki, Yoshinosuke
    Kang, Bubwoong
    Shinada, Tetsuro
    Satoh, Tetsuya
    CHEMISTRY-AN ASIAN JOURNAL, 2023, 18 (04)
  • [23] Synthesis of aryl ketones by the Pd-catalyzed C-H activation of arenes and intermolecular carbopalladation of nitriles
    Zhou, CX
    Larock, RC
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (08) : 2302 - 2303
  • [24] Pd-Catalyzed Aryl C-H Imidation with Arene as the Limiting Reagent
    Boursalian, Gregory B.
    Ngai, Ming-Yu
    Hojczyk, Katarzyna N.
    Ritter, Tobias
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (36) : 13278 - 13281
  • [25] Pd-catalyzed aryl C-H imidation with arene as the limiting reagent
    Ritter, T. (ritter@chemistry.harvard.edu), 1600, American Chemical Society (135):
  • [26] Dirhodium(II)-catalyzed intramolecular C-H amination of aryl azides
    Shen, Meihua
    Leslie, Brooke E.
    Driver, Tom G.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (27) : 5056 - 5059
  • [27] Pd(0)-Catalyzed Diarylation of sp3 C-H Bond in (2-Azaaryl)methanes
    Song, Guoyong
    Su, Yan
    Gong, Xue
    Han, Keli
    Li, Xingwei
    ORGANIC LETTERS, 2011, 13 (08) : 1968 - 1971
  • [28] Sequential Ruthenium(II)-Acetate Catalyzed C-H Bond Diarylation in NMP or Water and Hydrosilylation of Imines
    Li, Bin
    Bheeter, Charles B.
    Darcel, Christophe
    Dixneuf, Pierre H.
    TOPICS IN CATALYSIS, 2014, 57 (10-13) : 833 - 842
  • [29] Pd(II)-Catalyzed Synthesis of Benzisoxazolones from Benzohydroxamic Acids via C-H Activation
    Gao, Xi-Ai
    Yan, Ru-Long
    Wang, Xian-Xue
    Yan, Hao
    Li, Jian
    Guo, Han
    Huang, Guo-Sheng
    JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (17): : 7700 - 7705
  • [30] Enantioselective Synthesis of Atropisomeric Anilides via Pd(II)-Catalyzed Asymmetric C-H Olefination
    Yao, Qi-Jun
    Xie, Pei-Pei
    Wu, Yong-Jie
    Feng, Ya-Lan
    Teng, Ming-Ya
    Hong, Xin
    Shi, Bing-Feng
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (42) : 18266 - 18276