Palladium catalyzed 8-aminoimidazo[1,2-a]pyridine (AIP) directed selective β-C(sp2)-H arylation

被引：9
|
作者：
Mondal, Biswajit [1 ,2 ]
Ghosh, Prasanjit [2 ]
Kundu, MrinalKanti [1 ]
Das, Tapas Kumar [1 ,2 ]
Das, Sajal [2 ]
机构：
[1] TCG Life Sci Pvt Ltd, BN-7,Sect V, Kolkata 700091, India
[2] Univ North Bengal, Dept Chem, Darjeeling 734013, India
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2021年 / 19卷 / 02期
关键词：
H BOND ACTIVATION; CYCLIZATION; BIDENTATE; AUXILIARY; DESIGN; DERIVATIVES; SP(2);
D O I：
10.1039/d0ob02134b
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Palladium catalyzed arylation of the inert beta-C(sp(2))-H bond of carboxylic acid derivatives is reported herein for the first time utilizing 8-aminoimidazo[1,2-a]pyridine (AIP) as an efficacious and new inbuilt 6,5-fused bicyclic removable directing group. This protocol is scalable, exhibits high levels of beta-site selectivity and tolerates a broad spectrum of functional groups.
引用
收藏
页码：360 / 364
页数：5
相关论文
共 50 条
  • [1] 8-Aminoimidazo[1,2-a]pyridine (AIP) directed Pd(II) catalysis: site-selective ortho-C(sp2)-H arylation in aqueous medium
    Mondal, Biswajit
    Ghosh, Prasanjit
    Kundu, MrinalKanti
    Das, Sajal
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (07) : 1604 - 1609
  • [2] Copper(<sc>ii</sc>)-catalyzed, site-selective C(sp)2-H amination using 8-aminoimidazo[1,2-a]pyridine (8-AIP) as a directing group
    Hajra, Arun Kumar
    Ghosh, Prasanjit
    Roy, Chandrayee
    Kundu, Mrinalkanti
    Ghosh, Shibaji
    Das, Sajal
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (32) : 6617 - 6630
  • [3] Palladium-Catalyzed C(sp2)-H Arylation of Peptides Directed by Aspartic Acid
    Weng, Yiyi
    Zhan, Xuecheng
    Zhang, Yiyang
    Lin, Wen
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (04): : 2334 - 2343
  • [4] Pyridine-Directed Palladium-Catalyzed Phosphonation of C(sp2)-H Bonds
    Li, Changkun
    Yano, Takaaki
    Ishida, Naoki
    Murakami, Masahiro
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (37) : 9801 - 9804
  • [5] Pyridine-directed palladium-catalyzed electrochemical phosphonation of C(sp2)-H bond
    Grayaznova, Tatyana Vasilevna
    Dudkina, Yu. B.
    Islamov, D. R.
    Kataeva, O. N.
    Sinyashin, O. G.
    Vicic, D. A.
    Budnikova, Yu. H.
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2015, 785 : 68 - 71
  • [6] Palladium-Catalyzed sp2 C-H Arylation of Azoarenes with Arylhydrazines
    Li, Mingyang
    Ye, Yong
    CHEMCATCHEM, 2015, 7 (24) : 4137 - 4142
  • [7] Palladium-Catalyzed Arylation of C(sp2)-H Bonds with 2-(1-Methylhydrazinyl)pyridine as the Bidentate Directing Group
    Wei, Jian
    Shao, Xiaoru
    Zhao, Hua
    Yang, Hongjian
    Qiu, Shuxian
    Zhai, Hongbin
    ACS OMEGA, 2021, 6 (39): : 25151 - 25161
  • [8] COMPARED REACTIVITY OF 3-AMINOIMIDAZO[1,2-A]PYRIDINES, 5-AMINOIMIDAZO[1,2-A]PYRIDINES, 6-AMINOIMIDAZO[1,2-A]PYRIDINES, AND 8-AMINOIMIDAZO[1,2-A]PYRIDINES IN COMBES REACTION - ACCESS TO IMIDAZONAPHTHYRIDINES AND DIPYRIDO[1,2-A-3',2'-D]IMIDAZOLE
    BLACHE, Y
    GUEIFFIER, A
    CHAVIGNON, O
    VIOLS, H
    TEULADE, JC
    CHAPAT, JP
    HETEROCYCLES, 1994, 38 (07) : 1527 - 1532
  • [9] Palladium(II)-Catalyzed C(sp)-C(sp2) Coupling: A Direct Approach to Multi-Substituted Pyrrolo[1,2-a]pyrazines
    He, Chang
    Wang, Zijuan
    Chen, Yitong
    Zhang, Guolin
    Yu, Yongping
    SYNTHESIS-STUTTGART, 2021, 53 (12): : 2051 - 2056
  • [10] Palladium(II)-Catalyzed Regioselective Ortho Arylation of sp2 C?H Bonds of N-Aryl-2-amino Pyridine Derivatives
    Koley, Moumita
    Dastbaravardeh, Navid
    Schnuerch, Michael
    Mihovilovic, Marko D.
    CHEMCATCHEM, 2012, 4 (09) : 1345 - 1352
12345