C-H Activation/Metalation Approaches for the Synthesis of Indolizine Derivatives

被引:18
作者
Bertallo, Camila R. de S. [1 ]
Arroio, Thais R. [1 ]
Toledo, Monica F. Z. J. [1 ]
Sadler, Scott A. [2 ]
Vessecchi, Ricardo [3 ]
Steel, Patrick G. [2 ]
Clososki, Giuliano C. [1 ,3 ]
机构
[1] Univ Sao Paulo, Fac Ciencias Farmaceut Ribeirao Preto, Nucleo Pesquisas Prod Nat & Sintet, Av Cafe S-N, BR-14040903 Ribeirao Preto, SP, Brazil
[2] Univ Durham, Dept Chem, South Rd, Durham DH1 3LE, England
[3] Univ Sao Paulo, Fac Filosofia Ciencias & Letras Ribeirao Preto, Dept Quim, Av Bandeirantes 3900, BR-14040901 Ribeirao Preto, SP, Brazil
基金
英国工程与自然科学研究理事会; 巴西圣保罗研究基金会;
关键词
C-H borylation; Metalation; Indolizines; Cross-coupling; Heterocycles; ONE-POT; IRIDIUM COMPLEXES; BORYLATION; FUNCTIONALIZATION; FLUORESCENT; METALATION; AROMATICS; ZINCATION; MAGNESIUM; ARENES;
D O I
10.1002/ejoc.201900608
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The C-H borylation of indolizines has not previously been reported. In this communication, we describe our preliminary efforts to apply this chemistry to this scaffold and contrast this approach to directed metalation. Through these methodologies, it was possible obtain a library of substituted indolizines functionalized on both the pyridinic and pyrrole rings.
引用
收藏
页码:5205 / 5213
页数:9
相关论文
共 50 条
[31]   Efficient Synthesis of Frutinone A and Its Derivatives through Palladium-Catalyzed C-H Activation/Carbonylation [J].
Shin, Yongje ;
Yoo, Changho ;
Moon, Youngtaek ;
Lee, Yunho ;
Hong, Sungwoo .
CHEMISTRY-AN ASIAN JOURNAL, 2015, 10 (04) :878-881
[32]   C-H Activation of π-Arene Ruthenium Complexes [J].
Wilkinson, Luke A. ;
Pike, Jack A. ;
Walton, James W. .
ORGANOMETALLICS, 2017, 36 (22) :4376-4381
[33]   Sustainable metal catalysis in C-H activation [J].
Tzouras, Nikolaos V. ;
Stamatopoulos, Ioannis K. ;
Papastavrou, Argyro T. ;
Liori, Aggeliki A. ;
Vougioukalakis, Georgios C. .
COORDINATION CHEMISTRY REVIEWS, 2017, 343 :25-138
[34]   The ortho effect in directed C-H activation [J].
Toth, Balazs L. ;
Monory, Anna ;
Egyed, Orsolya ;
Domjan, Attila ;
Benyei, Attila ;
Szathury, Balint ;
Novak, Zoltan ;
Stirling, Andras .
CHEMICAL SCIENCE, 2021, 12 (14) :5152-5163
[35]   Electrochemical Oxidative C-H Amination of Phenols: Access to Triarylamine Derivatives [J].
Tang, Shan ;
Wang, Siyuan ;
Liu, Yichang ;
Cong, Hengjiang ;
Lei, Aiwen .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (17) :4737-4741
[36]   Access to Silylated Pyrazole Derivatives by Palladium-Catalyzed C-H Activation of a TMS group [J].
Mistico, Laetitia ;
Querolle, Olivier ;
Meerpoel, Lieven ;
Angibaud, Patrick ;
Durandetti, Muriel ;
Maddaluno, Jacques .
CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (28) :9687-9692
[37]   Synthesis of 8-azaprotosappanin A derivatives via intramolecular palladium-catalyzed ortho C-H activation/C-C cyclization and their antibacterial activity [J].
Zhou, Xuan ;
Fu, Wanyong ;
Jiang, Hongshuo ;
Wang, Chenglong ;
Ju, Chao ;
Chu, Wenyi ;
Sun, Zhizhong .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (09) :1955-1959
[38]   Functionalization of Porphyrins Using Metal-Catalyzed C-H Activation [J].
Kiselev, Aleksey N. ;
Syrbu, Sergey A. ;
Lebedeva, Natalia Sh ;
Gubarev, Yury A. .
INORGANICS, 2022, 10 (05)
[39]   Synthesis of Angiotensin II Receptor Blockers by Means of a Catalytic System for C-H Activation [J].
Seki, Masahiko ;
Nagahama, Masaki .
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (24) :10198-10206
[40]   Rhodium(III)-Catalyzed Synthesis of Naphthols via C-H Activation of Sulfoxonium Ylides [J].
Xu, Youwei ;
Yang, Xifa ;
Zhou, Xukai ;
Kong, Lingheng ;
Li, Xingwei .
ORGANIC LETTERS, 2017, 19 (16) :4307-4310