Palladium-Catalyzed Intermolecular Carbonylation-Based Difunctionalization of Alkenes

Bing Tian; Pinhong Chen; Guosheng Liu

doi:10.1055/s-0040-1719898

Synlett, Table of Contents

Synlett 2022; 33(10): 927-938
DOI: 10.1055/s-0040-1719898

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Palladium-Catalyzed Intermolecular Carbonylation-Based Difunctionalization of Alkenes

Bing Tian

^aState Key Laboratory of Organometallic Chemistry, and Shanghai Hongkong Joint Laboratory in Chemical Synthesis, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, P. R. of China

,

Pinhong Chen

^aState Key Laboratory of Organometallic Chemistry, and Shanghai Hongkong Joint Laboratory in Chemical Synthesis, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, P. R. of China

,

Guosheng Liu∗

^aState Key Laboratory of Organometallic Chemistry, and Shanghai Hongkong Joint Laboratory in Chemical Synthesis, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, P. R. of China

^bChang-Kung Chuang Institute, East China Normal University, 3663 North Zhongshan Road, Shanghai 200062, P. R. of China

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Abstract

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Abstract

The palladium(II)-catalyzed carbonylation of alkenes presents one of most efficient methods for the synthesis of alkyl-substituted carbonyls and has received much attention. In this Account, we summarize our recent studies on the palladium-catalyzed intermolecular carbonylation-based 1,2-difunctionalization of alkenes, in which two strategies were involved: (1) a cooperative strategy involves the sequential iodine(III)-mediated alkene activation and palladium-catalyzed carbonylation, leading to the intermolecular β-oxy-, fluoro-, and azidocarbonylation of alkenes; (2) the classic strategy initiated by intermolecular nucleopalladation and carbonylation, including the asymmetric oxycarbonylation of alkenes. These methods provide a series of efficient approaches to synthesize β-functionalized aliphatic carboxylic derivatives.

1 Introduction

2 A Cooperative Strategy Involving Iodine(III)-Mediated Alkene Activation and Palladium-Catalyzed Carbonylation

2.1 Intermolecular Oxycarbonylation of Alkenes

2.2 Intermolecular Fluorocarbonylation of Alkenes

2.3 Intermolecular Azidocarbonylation of Alkenes

3 Intermolecular Aminocarbonylation of Alkenes Initiated by Aminopalladation

4 Intermolecular Arylcarbonylation of Alkenes Initiated by Arylpalladation

5 Intermolecular Enantioselective Oxycarbonylation of Alkenes Initiated by Oxypalladation

6 Conclusion

Key words

difunctionalization - carbonylation - palladium catalysis - enantioselective - aminopalladation - arylpalladation - asymmetric oxypalladation

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