Azidofluoroalkylation of Alkenes with Simple Fluoroalkyl Iodides Enabled by Photoredox Catalysis

被引：94

作者：

Geng, Xiaoyu ^{[1
]}

Lin, Fengguirong ^{[1
]}

Wang, Xiaoyang ^{[1
]}

Jiao, Ning ^{[1
,2
]}

机构：

[1] Peking Univ, Sch Pharmaceut Sci, State Key Lab Nat & Biomimet Drugs, Xue Yuan Rd 38, Beijing 100191, Peoples R China

[2] East China Normal Univ, Shanghai Key Lab Green Chem & Chem Proc, Shanghai 200062, Peoples R China

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 18期

基金：

中国国家自然科学基金;

关键词：

C BOND-CLEAVAGE; DIOXYGEN ACTIVATION; VISIBLE-LIGHT; MEDICINAL CHEMISTRY; ALKYL AZIDES; AMINO-ACIDS; H AZIDATION; METAL-FREE; TRIFLUOROMETHYLATION; NITROGENATION;

D O I：

10.1021/acs.orglett.7b02056

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A mild and efficient protocol for photoredox-catalyzed azidofluoroalkylation of simple alkenes is described with readily available fluoroalkyl iodides. This method allows for a direct and regioselective formation of C-R-F and C-N-3 bonds from the C=C moiety. A variety of fluoroalkyl groups including the CF3 group can be selectively introduced to olefins to afford a series of,beta-fluoroalkylated azides.

引用

收藏

页码：4738 / 4741

页数：4

相关论文

共 64 条

[1]

[Anonymous], 2004, ChemBioChem, V5, P557

[2] Organic azides:: An exploding diversity of a unique class of compounds [J].

Bräse, S ;

Gil, C ;

Knepper, K ;

Zimmermann, V .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (33) :5188-5240

[3]

Cardona F, 2009, NAT CHEM, V1, P269, DOI [10.1038/nchem.256, 10.1038/NCHEM.256]

[4] v Catalytic Aminohalogenation of Alkenes and Alkynes [J].

Chemler, Sherry R. ;

Bovino, Michael T. .

ACS CATALYSIS, 2013, 3 (06) :1076-1091

[5] Mechanisms and applications of cyclometalated Pt(II) complexes in photoredox catalytic trifluoromethylation [J].

Choi, Won Joon ;

Choi, Sungkyu ;

Ohkubo, Kei ;

Fukuzumi, Shunichi ;

Cho, Eun Jin ;

You, Youngmin .

CHEMICAL SCIENCE, 2015, 6 (02) :1454-1464

[6] Photoredox-Induced Three-Component Azido- and Aminotrifluoromethylation of Alkenes [J].

Dagousset, Guillaume ;

Carboni, Aude ;

Magnier, Emmanuel ;

Masson, Geraldine .

ORGANIC LETTERS, 2014, 16 (16) :4340-4343

[7] Synthesis of novel paclitaxel prodrugs designed for bioreductive activation in hypoxic tumour tissue [J].

Damen, EWP ;

Nevalainen, TJ ;

van den Bergh, TJM ;

de Groot, FMH ;

Scheeren, HW .

BIOORGANIC & MEDICINAL CHEMISTRY, 2002, 10 (01) :71-77

[8] Enantioselective Iron-Catalyzed Azidation of β-Keto Esters and Oxindoles [J].

Deng, Qing-Hai ;

Bleith, Tim ;

Wadepohl, Hubert ;

Gade, Lutz H. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (14) :5356-5359

[9] Zidovudine azido-reductase in human liver microsomes: Activation by ethacrynic acid, dipyridamole, and indomethacin and inhibition by human immunodeficiency virus protease inhibitors [J].

Fayz, S ;

Inaba, T .

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1998, 42 (07) :1654-1658

[10] The many roles for fluorine in medicinal chemistry [J].

Hagmann, William K. .

JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (15) :4359-4369

← 1 2 3 4 5 6 7 →