Palladium-Catalyzed Spirocyclization through C-H Activation and Regioselective Alkyne Insertion

被引：129

作者：

Yoon, Hyung ^{[1
]}

Rolz, Martin ^{[1
]}

Landau, Felicitas ^{[1
]}

Lautens, Mark ^{[1
]}

机构：

[1] Univ Toronto, Davenport Chem Labs, Dept Chem, 80 St George St, Toronto, ON M5S 3H6, Canada

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2017年 / 56卷 / 36期

基金：

加拿大自然科学与工程研究理事会;

关键词：

alkynes; C-H activation; palladium; regioselectivity; spiro compounds; C(SP(2))-H BOND ACTIVATION; EFFICIENT SYNTHESIS; DOMINO REACTION; HECK REACTION; FUNCTIONALIZATION; OXINDOLES; ALKYLATION; C(SP(3))-H; MIGRATION; ARYLATION;

D O I：

10.1002/anie.201706325

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A Pd-catalyzed spirocyclization involving a sequential carbopalladation, intramolecular C-H activation, and a highly regioselective alkyne insertion to afford spirooxindoles and spirodihydrobenzofurans has been achieved. The spirocyclic products were generated in good to excellent yields with complete regiocontrol in a readily scalable procedure.

引用

页码：10920 / 10923

页数：4

共 51 条

[1] Aryl-aryl bond formation by transition-metal-catalyzed direct arylation [J].

Alberico, Dino ;

Scott, Mark E. ;

Lautens, Mark .

CHEMICAL REVIEWS, 2007, 107 (01) :174-238

[2] Ring Construction by Palladium(0)-Catalyzed C(sp3)-H Activation [J].

Baudoin, Olivier .

ACCOUNTS OF CHEMICAL RESEARCH, 2017, 50 (04) :1114-1123

[3] Pd-Catalyzed Dehydrogenative Aryl-Aryl Bond Formation via Double C(sp2)-H Bond Activation:, Efficient Synthesis of [3,4]-Fused Oxindoles [J].

Bunescu, Ala ;

Piou, Tiffany ;

Wang, Qian ;

Zhu, Jieping .

ORGANIC LETTERS, 2015, 17 (02) :334-337

[4]

Chen X., 2009, ANGEW CHEM, V121, P5196

[5] 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

[6] Transition metal-catalyzed C-H bond functionalizations by the use of diverse directing groups [J].

Chen, Zhengkai ;

Wang, Binjie ;

Zhang, Jitan ;

Yu, Wenlong ;

Liu, Zhanxiang ;

Zhang, Yuhong .

ORGANIC CHEMISTRY FRONTIERS, 2015, 2 (09) :1107-1295

[7] Pd/Norbornene: A Winning Combination for Selective Aromatic Functionalization via C-H Bond Activation [J].

Della Ca, Nicola ;

Fontana, Marco ;

Motti, Elena ;

Catellani, Marta .

ACCOUNTS OF CHEMICAL RESEARCH, 2016, 49 (07) :1389-1400

[8]

Garc?a-L?pez J.-A., 2016, ANGEW CHEM, V128, P14601

[9] Mild metal-catalyzed C-H activation: examples and concepts [J].

Gensch, T. ;

Hopkinson, M. N. ;

Glorius, F. ;

Wencel-Delord, J. .

CHEMICAL SOCIETY REVIEWS, 2016, 45 (10) :2900-2936

[10] Palladium-Catalysed, Directed C-H Coupling with Organometallics [J].

Giri, Ramesh ;

Thapa, Surendra ;

Kafle, Arjun .

ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (07) :1395-1411

← 1 2 3 4 5 6 →