Construction of unsymmetrical heterobiaryls via the Cp*Rh(iii)-catalysed C-H/C-H coupling of heteroarenes

被引：6

作者：

Parmar, Diksha ^{[1
,2
]}

Sharma, Tamanna ^{[1
]}

Sharma, Akhilesh K. K. ^{[3
]}

Sharma, Upendra ^{[1
,2
]}

机构：

[1] CSIR IHBT, Chem Technol Div, C H Activat & Phytochemistry Lab, Palampur 176061, India

[2] Acad Sci & Innovat Res AcSIR, Ghaziabad 201002, India

[3] Barcelona Inst Sci & Technol, Inst Chem Res Catalonia ICIQ CERCA, Ave Paisos Catalans,16, Tarragona 43007, Spain

来源：

CHEMICAL COMMUNICATIONS | 2023年 / 59卷 / 63期

关键词：

QUINOLINE N-OXIDES; FUNCTIONALIZATION; ACTIVATION; MECHANISM; INDOLES; ALKYNES; RHODIUM; ACCESS; AZOLES; BONDS;

D O I：

10.1039/d3cc03166g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Herein, a concise method for the Rh(iii)-catalyzed, directing-group-assisted C-H/C-H cross-coupling of N-heterocycles (quinolines, indolines, indoles, pyridines, pyrimidines, pyrazoles) with other heteroarenes (benzoxazoles, benzofurans, and thiophenes) is disclosed for the synthesis of unsymmetrical heterobiaryl compounds in good to excellent yields. A plausible catalytic cycle has been delineated based on experimental and computational mechanistic studies.

引用

页码：9646 / 9649

页数：4

共 50 条

[31] Pd-catalysed oxidative C-H/C-H coupling polymerization for polythiazole-based derivatives
Zhang, Qiang
Li, Yuefeng
Lu, Yan
Zhang, Huijing
Li, Miaomiao
Yang, Yang
Wang, Jing
Chen, Yongsheng
Li, Chenxi
POLYMER, 2015, 68 : 227 - 233
[32] Rh(<sc>iii</sc>)-catalyzed aldehydic and aryl C-H alkylation with cyclopropanols via C-H/C-C bond activation
Dash, Om Prakash
Garg, Divya
Volla, Chandra M. R.
CHEMICAL COMMUNICATIONS, 2024, 60 (76) : 10576 - 10579
[33] Rh(III)-Catalyzed C-H Activation/Annulation for the Construction of Quinolizinones and Indolizines
Hou, Xinjiao
Wang, Run
Fang, Feifei
Qu, Zhiyan
Zhou, Jianhui
Yu, Ting
Wang, Dechuan
Liu, Hong
Zhou, Yu
ORGANIC LETTERS, 2024, 26 (21) : 4451 - 4456
[34] Application of Ligands in Cp*Rh(III)-Catalyzed C-H Bond Functionalization Reaction
Pan Yannian
Qin Xiao
Yuan Chengkai
Lu Yi
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2023, 43 (03) : 924 - 948
[35] Cp*Rh(III)-Catalyzed C-H Bond Difluorovinylation of Indoles with α,α-Difluorovinyl Tosylate
Yang, Lisheng
Li, Chunpu
Wang, Dechuan
Liu, Hong
JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (11): : 7320 - 7330
[36] Enantioselective C-H Arylation for Axially Chiral Heterobiaryls
Liu, Ziyue
Gao, Ben
Chernichenko, Konstantin
Yang, He
Lemaire, Sebastien
Tang, Wenjun
ORGANIC LETTERS, 2023, 25 (38) : 7004 - 7008
[37] Copper-Mediated Intermolecular C-H/C-H and C-H/N-H Couplings via Aromatic C-H Cleavage
Hirano, Koji
Miura, Masahiro
C-H BOND ACTIVATION AND CATALYTIC FUNCTIONALIZATION II, 2016, 56 : 47 - 65
[38] Specific assembly of dihydrobenzofuran frameworks via Rh(iii)-catalysed C-H coupling of N-phenoxyacetamides with 2-alkenylphenols
Wei, Yinhui
Xu, Huiying
Chen, Fangyuan
Gao, Hui
Huang, Yugang
Yi, Wei
Zhou, Zhi
NEW JOURNAL OF CHEMISTRY, 2022, 46 (12) : 5705 - 5711
[39] Modern strategies for C-H functionalization of heteroarenes with alternative coupling partners
Zhao, Binlin
Prabagar, Baskaran
Shi, Zhuangzhi
CHEM, 2021, 7 (10): : 2585 - 2634
[40] Photoredox catalyzed C-H trifluoroethylamination of heteroarenes
Wang, Juan
Liu, Shuai
Huang, Yangen
Xu, Xiu-Hua
Qing, Feng-Ling
CHEMICAL COMMUNICATIONS, 2022, 58 (09) : 1346 - 1349

← 1 2 3 4 5 →