Pd-Catalyzed Olefination of Perfluoroarenes with Allyl Esters

被引：81

作者：

Li, Zejiang ^{[1
]}

Zhang, Yuexia ^{[1
]}

Liu, Zhong-Quan ^{[1
]}

机构：

[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Gansu, Peoples R China

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 01期

基金：

美国国家科学基金会;

关键词：

PROTON-ABSTRACTION MECHANISM; HIGHLY SELECTIVE ARYLATION; OXIDATIVE HECK REACTIONS; ARYLBORONIC ACIDS; BOND ACTIVATION; FUNCTIONALIZATION; FLUORINE; ARENES; ALKENYLATION; ALKYLATIONS;

D O I：

10.1021/ol202859b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient Pd(II)-catalyzed direct olefination of perfluoroarenes with allyl esters is demonstrated. Under the typical conditions, the coupling reaction of fluorinated-arenes with allylic esters proceeded via a beta-H elimination rather than a beta-OAc elimination to give the corresponding gamma-substituted allylic esters.

引用

页码：74 / 77

页数：4

共 59 条

[1] Direct arylations of electron-deficient (hetero)arenes with aryl or alkenyl tosylates and mesylates [J].

Ackermann, Lutz ;

Fenner, Sabine .

CHEMICAL COMMUNICATIONS, 2011, 47 (01) :430-432

[2] Catalytic system for heck reactions involving insertion into Pd-(perfluoro-organyl) bonds [J].

Albéniz, AC ;

Espinet, P ;

Martín-Ruiz, B ;

Milstein, D .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (46) :11504-11505

[3] C-F Bond Activation in Organic Synthesis [J].

Amii, Hideki ;

Uneyama, Kenji .

CHEMICAL REVIEWS, 2009, 109 (05) :2119-2183

[4] Synthesis and Reactivity of a Mono-σ-Aryl Palladium(IV) Fluoride Complex [J].

Ball, Nicholas D. ;

Sanford, Melanie S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (11) :3796-+

[5] PALLADIUM-CATALYZED VINYLATION OF ALLYLIC ALCOHOLS WITH ENOL TRIFLATES - A CONVENIENT SYNTHESIS OF CONJUGATED DIENOLS [J].

BERNOCCHI, E ;

CACCHI, S ;

CIATTINI, PG ;

MORERA, E ;

ORTAR, G .

TETRAHEDRON LETTERS, 1992, 33 (21) :3073-3076

[6] Selective Pd-catalyzed oxidative coupling of anilides with olefins through C-H bond activation at room temperature [J].

Boele, MDK ;

van Strijdonck, GPF ;

de Vries, AHM ;

Kamer, PCJ ;

de Vries, JG ;

van Leeuwen, PWNM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (08) :1586-1587

[7] Indirect ortho functionalization of substituted toluenes through ortho olefination of N,N-dimethylbenzylamines tuned by the acidity of reaction conditions [J].

Cai, Guixin ;

Fu, Ye ;

Li, Yizhou ;

Wan, Xiaobing ;

Shi, Zhangjie .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (24) :7666-7673

[8] Catalytic direct arylation with aryl chlorides, bromides, and iodides: Intramolecular studies leading to new intermolecular reactions [J].

Campeau, LC ;

Parisien, M ;

Jean, A ;

Fagnou, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (02) :581-590

[9] Palladium(II)-Catalyzed Selective Monofluorination of Benzoic Acids Using a Practical Auxiliary: A Weak-Coordination Approach [J].

Chan, Kelvin S. L. ;

Wasa, Masayuki ;

Wang, Xisheng ;

Yu, Jin-Quan .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (39) :9081-9084

[10] Palladium(II)-Catalyzed C-H Activation/C-C Cross-Coupling Reactions: Versatility and Practicality [J].

Chen, Xiao ;

Engle, Keary M. ;

Wang, Dong-Hui ;

Yu, Jin-Quan .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (28) :5094-5115

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