Cycloalkylation of C(sp3)-H Bond with Neighboring Carboxylic Acid as Traceless Activating Group

被引：26

作者：

Lv, Leiyang ^{[1
]}

Li, Zhiping ^{[1
]}

机构：

[1] Renmin Univ China, Dept Chem, Beijing 100872, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 82卷 / 05期

基金：

美国国家科学基金会;

关键词：

DIRECTING GROUPS; FUNCTIONALIZATION; CONSTRUCTION; ARYLATION; STRATEGY; PHOTOREDOX; CATALYSIS;

D O I：

10.1021/acs.joc.6b03091

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Selective functionalization of inert C(sp(3))-H bond is one of cutting-edge challenges in chemical synthesis. A novel strategy for selective C(sp(3))-H bond cydoalkylation is developed with neighboring carboxylic acid as a traceless activating group. Primary and secondary alkyl carboxylic acids undergo decarboxylation/alpha-C(sp(3))-H cleavage/cycloalkylation to give the five membered cyclization products, while tertiary adds undergo decarboxylation/ss-C(sp(3))-H cleavage/cycloalkylation to generate the six-membered cyclization products.

引用

页码：2689 / 2702

页数：14

共 42 条

[1] Photochemically induced radical alkenylation of C(sp3)-H bonds [J].

Amaoka, Yuuki ;

Nagatomo, Masanori ;

Watanabe, Mizuki ;

Tao, Keisuke ;

Kamijo, Shin ;

Inoue, Masayuki .

CHEMICAL SCIENCE, 2014, 5 (11) :4339-4345

[2] The catalytic intermolecular orthoarylation of phenols [J].

Bedford, RB ;

Coles, SJ ;

Hursthouse, MB ;

Limmert, ME .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (01) :112-114

[3] The Copper-Catalyzed Decarboxylative Coupling of the sp3-Hybridized Carbon Atoms of α-Amino Acids [J].

Bi, Hai-Peng ;

Zhao, Liang ;

Liang, Yong-Min ;

Li, Chao-Jun .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (04) :792-795

[4] Carboxylic Acids as Traceless Directing Groups for Formal meta-Selective Direct Arylation [J].

Cornella, Josep ;

Righi, Marika ;

Larrosa, Igor .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (40) :9429-9432

[5] Carboxylates as sources of carbon nucleophiles and electrophiles: comparison of decarboxylative and decarbonylative pathways [J].

Dzik, Wojciech I. ;

Lange, Paul P. ;

Goossen, Lukas J. .

CHEMICAL SCIENCE, 2012, 3 (09) :2671-2678

[6] Weak Coordination as a Powerful Means for Developing Broadly Useful C-H Functionalization Reactions [J].

Engle, Keary M. ;

Mei, Tian-Sheng ;

Wasa, Masayuki ;

Yu, Jin-Quan .

ACCOUNTS OF CHEMICAL RESEARCH, 2012, 45 (06) :788-802

[7] The Cross-Dehydrogenative Coupling of Csp3-H Bonds: A Versatile Strategy for C-C Bond Formations [J].

Girard, Simon A. ;

Knauber, Thomas ;

Li, Chao-Jun .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (01) :74-100

[8] C ∼ H Bond Functionalization through Intramolecular Hydride Transfer** [J].

Haibach, Michael C. ;

Seidel, Daniel .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (20) :5010-5036

[9] Evolution of C-H Bond Functionalization from Methane to Methodology [J].

Hartwig, John F. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (01) :2-24

[10] Copper-Catalyzed C-H Oxidative Radical Functionalization and Annulation of Aniline-Linked 1,7-Enynes: Evidence for a 1,5-Hydride Shift Mechanism [J].

Hu, Ming ;

Zou, Hua-Xu ;

Song, Ren-Jie ;

Xiang, Jian-Nan ;

Li, Jin-Heng .

ORGANIC LETTERS, 2016, 18 (24) :6460-6463

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