Product Divergence in Coinage-Metal-Catalyzed Reactions of π-Rich Compounds

被引：28

作者：

Boyle, Joshua William ^{[1
]}

Zhao, Yichao ^{[1
]}

Chan, Philip Wai Hong ^{[1
,2
]}

机构：

[1] Monash Univ, Sch Chem, Clayton, Vic 3800, Australia

[2] Univ Warwick, Dept Chem, Coventry CV4 7AL, W Midlands, England

来源：

SYNTHESIS-STUTTGART | 2018年 / 50卷 / 07期

基金：

澳大利亚研究理事会;

关键词：

coinage metals; copper; silver; gold; homogenous catalysis; product divergence; C-H FUNCTIONALIZATION; BOND FUNCTIONALIZATION; ALDER REACTION; PROPARGYLIC CARBOXYLATES; HETEROCYCLIC-COMPOUNDS; CASCADE CYCLIZATION; SELECTIVE SYNTHESIS; GOLD CATALYSIS; AMINO-ACIDS; SILVER;

D O I：

10.1055/s-0036-1591762

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This short review aims to summarize how the product outcome of reactions of a common starting material can sometimes be controlled by the judicious choice of copper, silver or gold as the catalyst. It highlights the different reactivities observed in the functional group transformations of -rich substrates mediated by the three group 11 metal salts. 1 Introduction 2 Reactions of Propargyl Amines, Esters and Their Derivatives 3 Reactions of Phenylacetylene Derivatives 4 Reactions of -Rich Alcohols and Ethers 5 Indolyl Cyclopropene and Alkynone Rearrangements 6 Reactions Involving Metal-Carbene and Metal-Carbenoid Intermediates 7 Conclusion

引用

页码：1402 / 1416

页数：15

共 107 条

[51] Silver catalyzed domino aza-annulation/Diels-Alder cyclization of 2-ene-yne anilines: a facile one-pot access to carbazole, dihydrocarbazole and tetrahydrocarbazole frameworks [J].

Krishna, Namballa Hari ;

Saraswati, A. Prasanth ;

Sathish, Manda ;

Shankaraiah, Nagula ;

Kamal, Ahmed .

CHEMICAL COMMUNICATIONS, 2016, 52 (24) :4581-4584

[52] Exploring the gold mine: [Au]-catalysed transformations of enynals, enynones and enynols [J].

Kumari, A. Leela Siva ;

Reddy, Alla Siva ;

Swamy, K. C. Kumara .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (28) :6651-6671

[53] Copper-Catalyzed Oxidation of Alkenes and Heterocycles [J].

Leticia Garcia-Cabeza, Ana ;

Javier Moreno-Dorado, F. ;

Ortega, Maria J. ;

Guerra, Francisco M. .

SYNTHESIS-STUTTGART, 2016, 48 (15) :2323-2342

[54] Silver-Catalyzed Reaction of Enynals with Alkenes: A Tandem 1,3-Dipolar Cycloaddition/Cyclopropanation [J].

Liang, Renxiao ;

Ma, Tongmei ;

Zhu, Shifa .

ORGANIC LETTERS, 2014, 16 (17) :4412-4415

[55] Catalyst-Driven Scaffold Diversity: Selective Synthesis of Spirocycles, Carbazoles and Quinolines from Indolyl Ynones [J].

Liddon, John T. R. ;

James, Michael J. ;

Clarke, Aimee K. ;

O'Brien, Peter ;

Taylor, Richard J. K. ;

Unsworth, William P. .

CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (26) :8777-8780

[56] Coinage Metal-N-Heterocyclic Carbene Complexes [J].

Lin, Joseph C. Y. ;

Huang, Roy T. W. ;

Lee, Chen S. ;

Bhattacharyya, Amitabha ;

Hwang, Wen S. ;

Lin, Ivan J. B. .

CHEMICAL REVIEWS, 2009, 109 (08) :3561-3598

[57] Copper-Catalyzed Synthesis of N-Heterocyclic Compounds [J].

Liu, Tao ;

Fu, Hua .

SYNTHESIS-STUTTGART, 2012, 44 (18) :2805-2824

[58] Advances in Copper-Catalyzed C-C Coupling Reactions and Related Domino Reactions Based on Active Methylene Compounds [J].

Liu, Yunyun ;

Wan, Jie-Ping .

CHEMISTRY-AN ASIAN JOURNAL, 2012, 7 (07) :1488-1501

[59] Luminescent aryl-group eleven metal complexes [J].

Lopez-de-Luzuriaga, Jose M. ;

Monge, Miguel ;

Elena Olmos, M. .

DALTON TRANSACTIONS, 2017, 46 (07) :2046-2067

[60] Gold-catalyzed para-selective C-H bond alkylation of benzene derivatives with donor/acceptor-substituted diazo compounds [J].

Ma, Ben ;

Wu, Jiaojiao ;

Liu, Lu ;

Zhang, Junliang .

CHEMICAL COMMUNICATIONS, 2017, 53 (73) :10164-10167

← 1 2 3 4 5 6 7 8 9 10 →