Rhodium(III)-Catalyzed Transannulation of Cyclopropenes with N-Phenoxyacetamides through C-H Activation

被引：175

作者：

Zhang, Hang ^{[1
,2
]}

Wang, Kang ^{[1
,2
]}

Wang, Bo ^{[1
,2
]}

Yi, Heng ^{[1
,2
]}

Hu, Fangdong ^{[1
,2
]}

Li, Changkun ^{[1
,2
]}

Zhang, Yan ^{[1
,2
]}

Wang, Jianbo ^{[1
,2
,3
]}

机构：

[1] Peking Univ, BNLMS, Coll Chem, Beijing 100871, Peoples R China

[2] Peking Univ, Key Lab Bioorgan Chem & Mol Engn, Minist Educ, Beijing 100871, Peoples R China

[3] Chinese Acad Sci, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2014年 / 53卷 / 48期

关键词：

carbenes; C-H activation; heterocycles; small ring compounds; rhodium; REGIOSELECTIVE SYNTHESIS; CATALYZED REARRANGEMENT; BOND ACTIVATION; ANNULATION; ALKYNES; ARYL; 2H-CHROMENES; METATHESIS; AMIDATION; OLEFINS;

D O I：

10.1002/anie.201408555

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An efficient rhodium(III)-catalyzed synthesis of 2H-chromene from N-phenoxyacetamides and cyclopropenes has been developed. The reaction represents the first example of using cyclopropenes as a three-carbon unit in rhodium(III)-catalyzed C(sp(2))-H activations.

引用

收藏

页码：13234 / 13238

页数：5

相关论文

共 69 条

[11] Rhodium Catalyzed Chelation-Assisted C-H Bond Functionalization Reactions [J].

Colby, Denise A. ;

Tsai, Andy S. ;

Bergman, Robert G. ;

Ellman, Jonathan A. .

ACCOUNTS OF CHEMICAL RESEARCH, 2012, 45 (06) :814-825

[12] Rhodium-Catalyzed C-C Bond Formation via Heteroatom-Directed C-H Bond Activation [J].

Colby, Denise A. ;

Bergman, Robert G. ;

Ellman, Jonathan A. .

CHEMICAL REVIEWS, 2010, 110 (02) :624-655

[13] Rh(III)-catalyzed C-H activation/[4+3] cycloaddition of benzamides and vinylcarbenoids: facile synthesis of azepinones [J].

Cui, Sunliang ;

Zhang, Yan ;

Wang, Dahai ;

Wu, Qifan .

CHEMICAL SCIENCE, 2013, 4 (10) :3912-3916

[14] C-H Functionalization in organic synthesis [J].

Davies, Huw M. L. ;

Du Bois, Justin ;

Yu, Jin-Quan .

CHEMICAL SOCIETY REVIEWS, 2011, 40 (04) :1855-1856

[15] Regioselectivity of the borylation of alkanes and arenes [J].

Hartwig, John F. .

CHEMICAL SOCIETY REVIEWS, 2011, 40 (04) :1992-2002

[16] Expedient Synthesis of N-Acyl Anthranilamides and β-Enamine Amides by the Rh(III)-Catalyzed Amidation of Aryl and Vinyl C-H Bonds with Isocyanates [J].

Hesp, Kevin D. ;

Bergman, Robert G. ;

Ellman, Jonathan A. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (30) :11430-11433

[17] Rhodium(III)-Catalyzed ortho Alkenylation of N-Phenoxyacetamides with N-Tosylhydrazones or Diazoesters through C-H Activation [J].

Hu, Fangdong ;

Xia, Ying ;

Ye, Fei ;

Liu, Zhenxing ;

Ma, Chen ;

Zhang, Yan ;

Wang, Jianbo .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (05) :1364-1367

[18] Rh(III)-Catalyzed C-H Activation and Double Directing Group Strategy for the Regioselective Synthesis of Naphthyridinones [J].

Huckins, John R. ;

Bercot, Eric A. ;

Thiel, Oliver R. ;

Hwang, Tsang-Lin ;

Bio, Matthew M. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (39) :14492-14495

[19] Rhodium(III)-Catalyzed C-H Activation Mediated Synthesis of Isoquinolones from Amides and Cyclopropenes [J].

Hyster, Todd K. ;

Rovis, Tomislav .

SYNLETT, 2013, 24 (14) :1842-1844

[20] A Coupling of Benzamides and Donor/Acceptor Diazo Compounds To Form γ-Lactams via Rh(III)-Catalyzed C-H Activation [J].

Hyster, Todd K. ;

Ruhl, Kyle E. ;

Rovis, Tomislav .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (14) :5364-5367

← 1 2 3 4 5 6 7 →