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Synlett 2022; 33(10): 927-938
DOI: 10.1055/s-0040-1719898
DOI: 10.1055/s-0040-1719898
account
Palladium-Catalyzed Intermolecular Carbonylation-Based Difunctionalization of Alkenes
We are grateful for financial support from the National Key Research and Development Program of China (2021YFA1500100), the National Natural Science Foundation of China (21971255, 21821002, 21790330, and 91956202), the Science and Technology Commission of Shanghai Municipality (19590750400, 21520780100, and 20JC1417000), the Key Research Program of Frontier Science ( QYZDJSSWSLH055), and the International Partnership Program of the Chinese Academy of Sciences (121731KYSB20190016).
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 oxypalladationPublication History
Received: 31 December 2021
Accepted after revision: 25 January 2022
Article published online:
15 February 2022
© 2022. Thieme. All rights reserved
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