Cu-Catalyzed C(sp3)-H Bond Activation Reaction for Direct Preparation of Cycloallyl Esters from Cycloalkanes and Aromatic Aldehydes

被引：74

作者：

Zhao, Jincan ^{[1
]}

Fang, Hong ^{[1
]}

Han, Jianlin ^{[1
,2
,3
]}

Pan, Yi ^{[1
]}

机构：

[1] Nanjing Univ, Sch Chem & Chem Engn, Nanjing 210093, Jiangsu, Peoples R China

[2] Nanjing Univ, High Tech Res Inst, Changzhou 213164, Peoples R China

[3] Nanjing Univ, Inst Chem & BioMed Sci, Nanjing 210093, Jiangsu, Peoples R China

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 09期

基金：

中国国家自然科学基金;

关键词：

TERT-BUTYL HYDROPEROXIDE; ALLYLIC OXIDATION; ALKANE-DEHYDROGENATION; RHENIUM COMPLEXES; COPPER; OLEFINS; ALKENES; ACYLOXYLATION; CYCLOHEXANE; PEROXIDES;

D O I：

10.1021/ol5009119

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cu-catalyzed dehydrogenation-olefination and esterification of C(sp(3))-H bonds of cycloalkanes with TBHP as an oxidant has been developed. The reaction involves four C-H bond activations and gives cycloallyl ester products directly from cycloalkanes and aromatic aldehydes.

引用

页码：2530 / 2533

页数：4

共 34 条

[1] Alkane Dehydrogenation by C-H Activation at Iridium(III) [J].

Allen, Kate E. ;

Heinekey, D. Michael ;

Goldman, Alan S. ;

Goldberg, Karen I. .

ORGANOMETALLICS, 2013, 32 (06) :1579-1582

[2] Copper catalyzed allylic oxidation with peresters [J].

Andrus, MB ;

Lashley, JC .

TETRAHEDRON, 2002, 58 (05) :845-866

[3] THE ACTIVATION OF C-H BONDS IN CYCLOALKANES BY RHENIUM COMPLEXES [J].

BAUDRY, D ;

EPHRITIKHINE, M ;

FELKIN, H .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1982, (11) :606-607

[4] SELECTIVE CATALYTIC DEHYDROGENATION OF ALKANES TO ALKENES [J].

BURK, MJ ;

CRABTREE, RH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (26) :8025-8032

[5]

Cavaliere V. N., 1999, J AM CHEM SOC, V121, P4086

[6] Room Temperature Dehydrogenation of Ethane to Ethylene [J].

Cavaliere, Vincent N. ;

Crestani, Marco G. ;

Pinter, Balazs ;

Pink, Maren ;

Chen, Chun-Hsing ;

Baik, Mu-Hyun ;

Mindiola, Daniel J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (28) :10700-10703

[7] Bu4NI-Catalyzed C-O Bond Formation by Using a Cross-Dehydrogenative Coupling (CDC) Reaction [J].

Chen, Long ;

Shi, Erbo ;

Liu, Zhaojun ;

Chen, Shulin ;

Wei, Wei ;

Li, Hong ;

Xu, Kai ;

Wan, Xiaobing .

CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (15) :4085-4089

[8] Dehydrogenation and Related Reactions Catalyzed by Iridium Pincer Complexes [J].

Choi, Jongwook ;

MacArthur, Amy H. Roy ;

Brookhart, Maurice ;

Goldman, Alan S. .

CHEMICAL REVIEWS, 2011, 111 (03) :1761-1779

[9] Introducing Copper as Catalyst for Oxidative Alkane Dehydrogenation [J].

Conde, Ana ;

Vilella, Laia ;

Balcells, David ;

Diaz-Requejo, M. Mar ;

Lledos, Agusti ;

Perez, Pedro J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (10) :3887-3896

[10]

Eames J, 2001, ANGEW CHEM INT EDIT, V40, P3567, DOI 10.1002/1521-3773(20011001)40:19<3567::AID-ANIE3567>3.0.CO

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