The Applications of Palladacycles as Transition-Metal Catalysts in Organic Synthesis

Dong-Liang Mo; Ting-Ke Zhang; Guang-Cun Ge; Xiao-Jun Huang; Chang-Hua Ding; Li-Xin Dai; Xue-Long Hou

doi:10.1055/s-0034-1379230

Synlett, Table of Contents

Synlett 2014; 25(19): 2686-2702
DOI: 10.1055/s-0034-1379230

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The Applications of Palladacycles as Transition-Metal Catalysts in Organic Synthesis

Dong-Liang Mo

^aState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling Ling Road, Shanghai 200032, P. R. of China Fax: +86(21)54925100 Email: xlhou@sioc.ac.cn Email: dingch@sioc.ac.cn

,

Ting-Ke Zhang

^cShanghai-Hong Kong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling Ling Road, Shanghai 200032, P. R. of China

,

Guang-Cun Ge

^aState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling Ling Road, Shanghai 200032, P. R. of China Fax: +86(21)54925100 Email: xlhou@sioc.ac.cn Email: dingch@sioc.ac.cn

,

Xiao-Jun Huang

^aState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling Ling Road, Shanghai 200032, P. R. of China Fax: +86(21)54925100 Email: xlhou@sioc.ac.cn Email: dingch@sioc.ac.cn

,

Chang-Hua Ding*

^aState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling Ling Road, Shanghai 200032, P. R. of China Fax: +86(21)54925100 Email: xlhou@sioc.ac.cn Email: dingch@sioc.ac.cn

,

Li-Xin Dai

^aState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling Ling Road, Shanghai 200032, P. R. of China Fax: +86(21)54925100 Email: xlhou@sioc.ac.cn Email: dingch@sioc.ac.cn

,

Xue-Long Hou*

^aState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling Ling Road, Shanghai 200032, P. R. of China Fax: +86(21)54925100 Email: xlhou@sioc.ac.cn Email: dingch@sioc.ac.cn

^cShanghai-Hong Kong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling Ling Road, Shanghai 200032, P. R. of China

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Abstract

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Abstract

This account summarizes our recent work on palladacycles in organic synthesis and describes some unique catalytic properties of palladacycles as transition-metal catalysts for some useful transformations. Asymmetric induction has been realized by using chiral palladacycles as transition-metal catalysts. The influence of the C−Pd bond of palladacycles on their catalytic activity has been revealed. The reaction selectivity can be switched by appropriate choice of an sp²- or sp³-hybridized C,P-palladacycle catalyst.

1 Introduction

2 The Discovery of the Use of Palladacycles as Transition-Metal Catalysts and Their Applications in Asymmetric Catalysis

3 Switch Between Addition and Ring Opening in the Reaction of Oxabicyclic Alkenes with Terminal Alkynes by Catalysis with sp²-C,P- or sp³-C,P-Palladacycles

4 Synthesis of Polysubstituted Furans, Methylenecyclopropanes, and Polycyclic 5H-Benzo[b]azepines through Catalysis by Palladacycles

5 Conclusions

Key words

palladacycles - transition metals - catalysis - asymmetric catalysis - bicyclic compounds - alkenes

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References

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