Ligand-free Pd-catalyzed highly selective arylation of allylic esters with retention of the traditional leaving group

被引：85

作者：

Pan, Delin ^{[1
]}

Chen, Anjun ^{[2
]}

Su, Yijin ^{[1
]}

Zhou, Wang ^{[1
]}

Li, Si ^{[1
]}

Jia, Wei ^{[1
]}

Xiao, Juan ^{[1
]}

Liu, Qingjian ^{[2
]}

Zhang, Liangren ^{[1
]}

Jiao, Ning ^{[1
]}

机构：

[1] Peking Univ, Sch Pharmaceut Sci, State Key Lab Nat & Biomimet Drugs, Beijing 100083, Peoples R China

[2] Shandong Normal Univ, Dept Chem, Jinan 250014, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2008年 / 47卷 / 25期

关键词：

allylic compounds; Heck reaction; palladium; regioselectivity; silver;

D O I：

10.1002/anie.200800966

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) What leaving group? Organic halides and allylic esters undergo efficient Pd-catalyzed Heck reactions under mild conditions in air to form a new C-C bond without elimination of the β-OAc group in the intermediate palladium complex. Instead a highly regioselective β-H elimination takes place to provide substituted derivatives of allylic alcohols (see scheme). © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：4729 / 4732

页数：4

共 71 条

[1] INTRAMOLECULAR ALKENE ARYLATIONS FOR RAPID ASSEMBLY OF POLYCYCLIC SYSTEMS CONTAINING QUATERNARY CENTERS - A NEW SYNTHESIS OF SPIROOXINDOLES AND OTHER FUSED AND BRIDGED RING-SYSTEMS [J].

ABELMAN, MM ;

OH, T ;

OVERMAN, LE .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (18) :4130-4133

[2] Anionic Pd(0) and Pd(II) intermediates in palladium-catalyzed Heck and cross-coupling reactions [J].

Amatore, C ;

Jutand, A .

ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (05) :314-321

[3]

[Anonymous], 2002, J ORGANOMET CHEM

[4] PALLADIUM IN SOME SELECTIVE OXIDATION REACTIONS [J].

BACKVALL, JE .

ACCOUNTS OF CHEMICAL RESEARCH, 1983, 16 (09) :335-342

[5] The development of palladium catalysts for C-C and C-heteroatom bond forming reactions of aryl chloride substrates [J].

Bedford, RB ;

Cazin, CSJ ;

Holder, D .

COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) :2283-2321

[6] The heck reaction as a sharpening stone of palladium catalysis [J].

Beletskaya, IP ;

Cheprakov, AV .

CHEMICAL REVIEWS, 2000, 100 (08) :3009-3066

[7] 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

[8]

Bräse S, 1998, SYNTHESIS-STUTTGART, P148

[9] RECENT DEVELOPMENTS AND NEW PERSPECTIVES IN THE HECK REACTION [J].

CABRI, W ;

CANDIANI, I .

ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (01) :2-7

[10] 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

← 1 2 3 4 5 6 7 8 →