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
  • [31] Pd(ii)-catalyzed selective β-C-H functionalization of azobenzene carboxamides
    Padmavathi, Rayavarapu
    Babu, Srinivasarao Arulananda
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (13) : 2689 - 2694
  • [32] Computational exploration of Pd(II)-catalyzed C-H activation and functionalization
    Yang, Yunfang
    Houk, Kendall
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 254
  • [33] Concise synthesis of pyrrolophenanthridine alkaloids using a Pd-catalyzed biaryl coupling reaction with regioselective C-H activation
    Harayama, T
    Hori, A
    Abe, H
    Takeuchi, Y
    HETEROCYCLES, 2003, 60 (11) : 2429 - 2434
  • [34] Pd(II)-Catalyzed Enantioselective C-H Olefination of Diphenylacetic Acids
    Shi, Bing-Feng
    Zhang, Yang-Hui
    Lam, Jonathan K.
    Wang, Dong-Hui
    Yu, Jin-Quan
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (02) : 460 - +
  • [35] Computational Exploration of a Pd(II)-Catalyzed γ-C-H Arylation Where Stereoselectivity Arises from Attractive Aryl-Aryl Interactions
    Bay, Katherine L.
    Yang, Yun-Fang
    Houk, K. N.
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (23): : 14786 - 14790
  • [36] Pd(H)-Catalyzed C-H Amination for N-Heterocyclic Synthesis
    Jeong, Eun Joo
    Youn, So Won
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2014, 35 (09) : 2611 - 2612
  • [37] Copper-Mediated Selective Mono- and Sequential Organochalcogenation of C-H Bonds: Synthesis of Hybrid Unsymmetrical Aryl Ferrocene Chalcogenides
    Sattar, Moh.
    Patidar, Krishna
    Thorat, Raviraj Ananda
    Kumar, Sangit
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (11): : 6669 - 6678
  • [38] Pd/C-Catalyzed Synthesis of Isoquinolones through C-H Activation
    Shu, Zhen
    Li, Wei
    Wang, Baiquan
    CHEMCATCHEM, 2015, 7 (04) : 605 - 608
  • [39] Mono- and bis-norbornene annulated biarylamines through pseudo-Catellani intermediates by Pd-catalyzed C-H activation
    Chuang, Shih-Ching
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 258
  • [40] Merging C-H and C-C Activation in Pd(II)-Catalyzed Enantioselective Synthesis of Axially Chiral Biaryls
    Chen, Hao-Ming
    Liao, Gang
    Xu, Cheng-Kai
    Yao, Qi-Jun
    Zhang, Shuo
    Shi, Bing-Feng
    CCS CHEMISTRY, 2021, 3 (12): : 455 - 465