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

被引：17

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

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 2019卷 / 31-32期

基金：

巴西圣保罗研究基金会; 英国工程与自然科学研究理事会;

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

页码：5205 / 5213

页数：9

共 50 条

[1] Iridium-Catalyzed C-H Activation versus Directed ortho Metalation: Complementary Borylation of Aromatics and Heteroaromatics
Hurst, Timothy E.
Macklin, Todd K.
Becker, Maike
Hartmann, Eduard
Kuegel, Wolfgang
Parisienne-La Salle, Jean-Christophe
Batsanov, Andrei S.
Marder, Todd B.
Snieckus, Victor
CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (27) : 8155 - 8161
[2] Photocatalytic Synthesis of Oxetane Derivatives by Selective C-H Activation
Ravelli, Davide
Zoccolillo, Matteo
Mella, Mariella
Fagnoni, Maurizio
ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (13) : 2781 - 2786
[3] C-H Metalation Reaction of Diarylamine and Carbazole by Alkylaluminum Complexes at the Heteroatom-Bridged Dimeric Aluminum Core
Yamamoto, Koji
Shibata, Yu
Kashiwa, Yuki
Kondo, Ai
Tsurugi, Hayato
Mashima, Kazushi
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2013, 2013 (22-23) : 3821 - 3825
[4] C-H Activation: A Versatile Tool for the Synthesis of Niclosamide and Its Derivatives
Gundamalla, Rachel
Bantu, Rajashaker
Sridhar, B.
Reddy, B. . V. Subba
SYNLETT, 2024, 35 (20) : 2520 - 2524
[5] Solvent-Free Ruthenium(II)-Catalyzed C-H Activation: Synthesis of Alkenylarylpyrazole Derivatives
Shome, Sanchari
Singh, Surya Prakash
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (27) : 6025 - 6032
[6] Iridium(III)-Catalyzed Synthesis of Benzimidazoles via C-H Activation and Amidation of Aniline Derivatives
Xia, Jintao
Yang, Xifa
Li, Yunyun
Li, Xingwei
ORGANIC LETTERS, 2017, 19 (12) : 3243 - 3246
[7] Direct Dimesitylborylation of Benzofuran Derivatives by an Iridium-Catalyzed C-H Activation with Silyldimesitylborane
Shishido, Ryosuke
Sasaki, Ikuo
Seki, Tomohiro
Ishiyama, Tatsuo
Ito, Hajime
CHEMISTRY-A EUROPEAN JOURNAL, 2019, 25 (56) : 12924 - 12928
[8] Rhodium(III)-Catalyzed Synthesis of Spiropiperidine Derivatives via C-H Activation
Peneau, Augustin
Retailleau, Pascal
Guillou, Catherine
Chabaud, Laurent
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (04) : 2324 - 2340
[9] Synthesis of Ferrocene 1,3-Derivatives by Distal C-H Activation
Gupta, Princi
Madhavan, Suchithra
Kapur, Manmohan
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (34)
[10] The synthesis of 2- and 2,7-functionalized pyrene derivatives through Ru(II)-catalyzed C-H activation
He, Yan-Qin
Zhong, Yu-Wu
CHEMICAL COMMUNICATIONS, 2015, 51 (16) : 3411 - 3414

← 1 2 3 4 5 →