Ruthenium(II)-catalyzed para-selective C??H difluoroalkylation of aromatic aldehydes and ketones using transient directing groups

被引：40

作者：

Cheng, Yaohang ^{[1
]}

He, Yuhang ^{[1
]}

Zheng, Jie ^{[1
]}

Yang, Hui ^{[1
]}

Liu, Jun ^{[1
]}

An, Guanghui ^{[1
,2
]}

Li, Guangming ^{[1
]}

机构：

[1] Heilongjiang Univ, Sch Chem & Mat Sci, Key Lab Funct Inorgan Mat Chem MOE, Harbin 150080, Peoples R China

[2] Harbin Engn Univ, Coll Mat Sci & Chem Engn, Harbin 150001, Peoples R China

来源：

CHINESE CHEMICAL LETTERS | 2021年 / 32卷 / 04期

关键词：

para-Selectivity; Difluoroalkylation; Ruthenium catalysis; C-H activation; ARYL BORONIC ACIDS; CATALYZED DIFLUOROALKYLATION; H DIFLUOROMETHYLATION; BENZALDEHYDES; META; FUNCTIONALIZATION; ARENES; ALKYLATION; AMIDATION; ACCESS;

D O I：

10.1016/j.cclet.2020.09.044

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A Ru(II)-catalyzed para-difluoroalkylation of aromatic aldehydes and ketones with a transient directing group has been developed. It utilizes less expensive ruthenium catalysts and allows facile access to challenging difluoroalkylated aldehydes. The mechanism studies suggest that the distinct coordination mode of ruthenium complex with imine moieties is responsible for para-selectivity. ? 2020 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

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收藏

页码：1437 / 1441

页数：5

相关论文

共 59 条

[1] Nanomolar Potency and Metabolically Stable Inhibitors of Kidney Urea Transporter UT-B [J].

Anderson, Marc O. ;

Zhang, Jicheng ;

Liu, Yan ;

Yao, Chenjuan ;

Phuan, Puay-Wah ;

Verkrnan, A. S. .

JOURNAL OF MEDICINAL CHEMISTRY, 2012, 55 (12) :5942-5950

[2] Regiodivergent Visible Light-Induced C-H Functionalization of Quinolines at C-5 and C-8 under Metal-, Photosensitizer- and Oxidant-Free Conditions [J].

Arockiam, Percia Beatrice ;

Guillemard, Lucas ;

Wencel-Delord, Joanna .

ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (15) :2571-2579

[3] Copper-Catalyzed Innate Ethoxycarbonyldifluoromethylation of Electron-Rich Arenes [J].

Belhomme, Marie-Charlotte ;

Bayle, Alexandre ;

Poisson, Thomas ;

Pannecoucke, Xavier .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (08) :1719-1726

[4] Copper-Catalyzed Direct C-2 Difluoromethylation of Furans and Benzofurans: Access to C-2 CF2H Derivatives [J].

Belhomme, Marie-Charlotte ;

Poisson, Thomas ;

Pannecoucke, Xavier .

JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (15) :7205-7211

[5] MONOFLUORO-METHYLENEBISPHOSPHONIC AND DIFLUORO-METHYLENEBISPHOSPHONIC ACIDS - ISOPOLAR ANALOGS OF PYROPHOSPHORIC ACID [J].

BLACKBURN, GM ;

ENGLAND, DA ;

KOLKMANN, F .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (17) :930-932

[6] Ruthenium-Catalyzed Difluoroalkylation of 8-Aminoquinoline Amides at the C5-Position [J].

Chen, Changpeng ;

Zeng, Runsheng ;

Zhang, Jingyu ;

Zhao, Yingsheng .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (46) :6947-6950

[7] Nickel-Catalyzed Site-Selective C-H Bond Difluoroalkylation of 8-Aminoquinolines on the C5-Position [J].

Chen, Hao ;

Li, Pinhua ;

Wang, Min ;

Wang, Lei .

ORGANIC LETTERS, 2016, 18 (19) :4794-4797

[8] Ir(iii)-catalyzed ortho C-H alkylations of (hetero)aromatic aldehydes using alkyl boron reagents [J].

Chen, Xiao-Yang ;

Sorensen, Erik J. .

CHEMICAL SCIENCE, 2018, 9 (48) :8951-8956

[9] Pd-Catalyzed, ortho C-H Methylation and Fluorination of Benzaldehydes Using Orthanilic Acids as Transient Directing Groups [J].

Chen, Xiao-Yang ;

Sorensen, Erik J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (08) :2789-2792

[10] Pd-Catalyzed Ortho C-H Hydroxylation of Benzaldehydes Using a Transient Directing Group [J].

Chen, Xiao-Yang ;

Ozturk, Seyma ;

Sorensen, Erik J. .

ORGANIC LETTERS, 2017, 19 (23) :6280-6283

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