Photoredox C-F Quaternary Annulation Catalyzed by a Strongly Reducing Iridium Species

被引：37

作者：

Dai, Peng ^{[1
,2
]}

Ma, Junyu ^{[2
]}

Huang, Wenhao ^{[2
]}

Chen, Wenxin ^{[2
]}

Wu, Na ^{[2
]}

Wu, Shengfu ^{[2
]}

Li, Ying ^{[2
]}

Cheng, Xu ^{[2
,3
,4
]}

Tan, Renxiang ^{[1
,3
]}

机构：

[1] Nanjing Univ, Inst Funct Biomol, State Key Lab Pharmaceut Biotechnol, Nanjing 210023, Jiangsu, Peoples R China

[2] Nanjing Univ, Jiangsu Key Lab Adv Organ Mat, Sch Chem & Chem Engn, Inst Chem & Biomed Sci, Nanjing 210023, Jiangsu, Peoples R China

[3] Nanjing Univ Chinese Med, State Key Lab Cultivat Base TCM Qual & Efficacy, Nanjing 210023, Jiangsu, Peoples R China

[4] Nankai Univ, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China

来源：

ACS CATALYSIS | 2018年 / 8卷 / 02期

基金：

美国国家科学基金会;

关键词：

annulation; C-F bond activation; quaternary alkylation; photocatalysis; stereoconvergence; VISIBLE-LIGHT PHOTOREDOX; ELECTRON-TRANSFER; ARYL HALIDES; C(SP(3))-H FUNCTIONALIZATION; H ACTIVATION; ARYLATION; 1,10-PHENANTHROLINE; HYDRODEFLUORINATION; SUBSTITUTION; GENERATION;

D O I：

10.1021/acscatal.7b03089

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

We report a fac-Ir (ppy)(3)*-Ir-II-Ir-III photocatalytic cycle involving t-BuOK as the terminal reductant in a visible-light-induced sp(2) C-F quaternary annulation reaction that proceeds in yields up to 98%. Because of the high activity of the Ir-II(ppy)(3) catalyst, even at a loading of 50 ppm, the annulation reaction was able to compete with anuncatalyzed nucleophilic aromatic substitution reaction. The annulation reaction was stereoconvergent, and an annulated product was synthesized with complete retention of enantiomeric excess.

引用

页码：802 / 806

页数：5

共 28 条

[1] Visible Light Photocatalysis for the Generation and Use of Reactive Azolyl and Polyfluoroaryl Intermediates [J].

Arora, Amandeep ;

Weaver, Jimmie D. .

ACCOUNTS OF CHEMICAL RESEARCH, 2016, 49 (10) :2273-2283

[2] KOtBu-Mediated Synthesis of Dimethylisoindolin-1-ones and Dimethyl-5-phenylisoindolin-1-ones: Selective C-C Coupling of an Unreactive Tertiary sp3 C-H Bond [J].

Bhakuni, Bhagat Singh ;

Yadav, Abhimanyu ;

Kumar, Shailesh ;

Patel, Saket ;

Sharma, Shubham ;

Kumar, Sangit .

JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (07) :2944-2954

[3] Intramolecular 1,5-H transfer reaction of aryl iodides through visible-light photoredox catalysis: a concise method for the synthesis of natural product scaffolds [J].

Chen, Jian-Qiang ;

Wei, Yun-Long ;

Xu, Guo-Qiang ;

Liang, Yong-Min ;

Xu, Peng-Fei .

CHEMICAL COMMUNICATIONS, 2016, 52 (38) :6455-6458

[4] Visible-Light Photoredox in Homolytic Aromatic Substitution: Direct Arylation of Arenes with Aryl Halides [J].

Cheng, Yannan ;

Gu, Xiangyong ;

Li, Pixu .

ORGANIC LETTERS, 2013, 15 (11) :2664-2667

[5] β-Selective Reductive Coupling of Alkenylpyridines with Aldehydes and Imines via Synergistic Lewis Acid/Photoredox Catalysis [J].

Lee, Katarzyna N. ;

Lei, Zhen ;

Ngai, Ming-Yu .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (14) :5003-5006

[6] Visible-Light-Mediated Two-Fold Unsymmetrical C(sp3)-H Functionalization and Double C-F Substitution [J].

Li, Linyong ;

Xiao, Tiebo ;

Chen, Haoguo ;

Zhou, Lei .

CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (10) :2249-2254

[7] Organocatalysis in Cross-Coupling: DMEDA-Catalyzed Direct C-H Arylation of Unactivated Benzene [J].

Liu, Wei ;

Cao, Hao ;

Zhang, Hua ;

Zhang, Heng ;

Chung, Kin Ho ;

He, Chuan ;

Wang, Haibo ;

Kwong, Fuk Yee ;

Lei, Aiwen .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (47) :16737-16740

[8] Potassium tert-Butoxide-Catalyzed Dehydrogenative C-H Silylation of Heteroaromatics: A Combined Experimental and Computational Mechanistic Study [J].

Liu, Wen-Bo ;

Schuman, David P. ;

Yang, Yun-Fang ;

Toutov, Anton A. ;

Liang, Yong ;

Klare, Hendrik F. T. ;

Nesnas, Nasri ;

Oestreich, Martin ;

Blackmond, Donna G. ;

Virgil, Scott C. ;

Banerjee, Shibdas ;

Zare, Richard N. ;

Grubbs, Robert H. ;

Houk, K. N. ;

Stoltz, Brian M. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (20) :6867-6879

[9] Light induced catalytic hydrodefluorination of perfluoroarenes by porphyrin rhodium [J].

Liu, Xu ;

Wang, Zikuan ;

Zhao, Xianyuan ;

Fu, Xuefeng .

INORGANIC CHEMISTRY FRONTIERS, 2016, 3 (06) :861-865

[10] The Acetal Concept: Regioselective Access to ortho,ortho-Diphenols via Dibenzo-1,3-dioxepines [J].

Masters, Kye-Simeon ;

Braese, Stefan .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (03) :866-869

← 1 2 3 →