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Synlett 2022; 33(09): 805-814
DOI: 10.1055/s-0040-1719877
DOI: 10.1055/s-0040-1719877
synpacts
Palladium-Catalyzed Site-Selective Arylation of α,β-Unsaturated Carbonyl Compounds through a Ligand-Controlled Strategy
We thank the Research Grants Council of the Hong Kong Special Administrative Region, China (PolyU 25301819 and 15300220), the National Natural Science Foundation of China (21972122), and Shenzhen Municipal Science and Technology Innovation Commission (JCYJ20180306173843318) for financial support.
Abstract
Palladium-catalyzed direct arylation of α,β-unsaturated carbonyl compounds is an efficient and attractive strategy to access arylated α,β-unsaturated carbonyl compounds through the construction of carbon–carbon bonds. This reaction has several challenges, especially in terms of the control of regioselectivity between α- and γ-arylation and the selectivity for monoarylation and multiple arylation. Herein, we discuss the recent development of γ-arylation of α,β-unsaturated carbonyl compounds and present the ligand-controlled, site-selective α- and γ-arylation of α,β-unsaturated carbonyl ketones with (hetero)aryl halides. The site selectivity of the reaction is switchable by simply changing the phosphine ligand.
1 Introduction
2 Reaction Development and Mechanistic Investigation
3 Conclusion and Outlook
Key words
palladium catalysis - phosphine ligand - regioselectivity - arylation - α,β-unsaturated ketonesPublication History
Received: 05 December 2021
Accepted after revision: 23 December 2021
Article published online:
01 February 2022
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