Directing group migration strategy in transition-metal-catalysed direct C-H functionalization

被引：124

作者：

Wu, Yingtao ^{[1
,2
]}

Pi, Chao ^{[1
]}

Wu, Yangjie ^{[1
,2
]}

Cui, Xiuling ^{[1
]}

机构：

[1] Zhengzhou Univ, Key Lab Appl Chem Henan Univ, Henan Key Lab Chem Biol & Organ Chem, Green Catalysis Ctr, Zhengzhou 450052, Peoples R China

[2] Zhengzhou Univ, Coll Chem, Zhengzhou 450052, Peoples R China

来源：

CHEMICAL SOCIETY REVIEWS | 2021年 / 50卷 / 06期

关键词：

QUINOLINE N-OXIDES; DIRECT ARYLATION; INDOLE SYNTHESIS; ACTIVATION; ALKYNES; PHENOXYACETAMIDES; CARBOAMINATION; CYCLIZATION; ALKENES; BOND;

D O I：

10.1039/d0cs00966k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Very recently, directing group (DG) migration has emerged as a practical strategy for transition-metal-catalysed direct C-H activation, resulting in a highly atom-economical process and enabling the reusage of DG. Therefore, great progress has been made in developing multitasking DGs. In this tutorial review, we present the rapid advances of this novel strategy by analyzing and comparing the different types of migratabIe DGs (including N-O, N-C, N-N or O-C bond cleavage to trigger DG migration). The related mechanisms, as well as synthetic applications, are also mentioned.

引用

页码：3677 / 3689

页数：13

共 44 条

[1] Palladium-catalyzed benzofuran and indole synthesis by multiple C-H functionalizations [J].

Agasti, Soumitra ;

Dey, Aniruddha ;

Maiti, Debabrata .

CHEMICAL COMMUNICATIONS, 2017, 53 (49) :6544-6556

[2] Transition Metal Promoted Cascade Heterocycle Synthesis through C-H Functionalization [J].

Baccalini, Alessio ;

Faita, Giuseppe ;

Zanoni, Giuseppe ;

Maiti, Debabrata .

CHEMISTRY-A EUROPEAN JOURNAL, 2020, 26 (44) :9749-9783

[3] Cobalt(III) catalyzed C-8 selective C-H and C-O coupling of quinoline N-oxide with internal alkynes via C-H activation and oxygen atom transfer [J].

Barsu, Nagaraju ;

Sen, Malay ;

Premkumar, J. Richard ;

Sundararaju, Basker .

CHEMICAL COMMUNICATIONS, 2016, 52 (07) :1338-1341

[4] A solution to the 2-pyridyl organometallic cross-coupling problem:: Regioselective catalytic direct arylation of pyridine N-oxides [J].

Campeau, LC ;

Rousseaux, S ;

Fagnou, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (51) :18020-18021

[5] Regioselective indole C2-alkylation using -CF3-substituted enones under redox neutral Rh(iii) catalysis [J].

Chaudhary, Bharatkumar ;

Diwaker, Monika ;

Sharma, Satyasheel .

ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (21) :3133-3137

[6] Manganese(I)-Catalyzed Regio- and Stereoselective 1,2-Diheteroarylation of Allenes: Combination of C-H Activation and Smiles Rearrangement [J].

Chen, Shi-Yong ;

Han, Xiang-Lei ;

Wu, Jia-Qiang ;

Li, Qingjiang ;

Chen, Yunyun ;

Wang, Honggen .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (33) :9939-9943

[7] A multitasking functional group leads to structural diversity using designer C-H activation reaction cascades [J].

Chen, Ying ;

Wang, Dongqi ;

Duan, Pingping ;

Ben, Rong ;

Dai, Lu ;

Shao, Xiaoru ;

Hong, Mei ;

Zhao, Jing ;

Huang, Yong .

NATURE COMMUNICATIONS, 2014, 5

[8] Palladium-catalyzed C-H functionalization of pyridine N-oxides:: Highly selective alkenylation and direct arylation with unactivated arenes [J].

Cho, Seung Hwan ;

Hwang, Seung Jun ;

Chang, Sukbok .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (29) :9254-+

[9] Selective Cyclization of Arylnitrones to Indolines under External Oxidant-Free Conditions: Dual Role of Rh(III) Catalyst in the C-H Activation and Oxygen Atom Transfer [J].

Dateer, Ramesh B. ;

Chang, Sukbok .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (15) :4908-4911

[10] I2-Mediated Iodization/[3+2] Cycloaddition/Nucleophilic Addition Tandem Reaction: Synthesis of Polyheterocycles Bearing Furoquinoline and Maleimide [J].

Du, Sidong ;

Pi, Chao ;

Wan, Ting ;

Wu, Yangjie ;

Cu, Xiuling .

ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (08) :1766-1770

← 1 2 3 4 5 →