Recent advances in ligand-enabled palladium-catalyzed divergent synthesis

Wang, Yue; Feng, Jinzan; Li, Er-Qing; Jia, Zhenhua; Loh, Teck-Peng

doi:10.1039/d3ob01679j

Org. Biomol. Chem.

2024

DOI: 10.1039/d3ob01679j

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Recent advances in ligand-enabled palladium-catalyzed divergent synthesis

Yue Wang,

Jinzan Feng,

Er-Qing Li

et al.

Abstract: In this review, recent advances in ligand-enabled palladium-catalyzed divergent synthesis are reported.

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Cited by 2 publications

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Functional-Group-Directed Regiodivergent (3 + 2) Annulations of Electronically Distinct 1,3-Dienes and 2-Formyl Arylboronic Acids

Liang,

Zhang,

Chen

et al. 2024

Org. Lett.

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Presented herein is a palladium-catalyzed asymmetric (3 + 2) annulation reaction between 1,3-dienes and 2formylarylboronic acids, proceeding in a cascade vinylogous addition and Suzuki coupling process. Both electron-neutral and electron-deficient 1,3-dienes are compatible under similar catalytic conditions, and distinct regioselectivity is observed via functionalgroup control of 1,3-diene substrates. A collection of 1-indanols with dense functionalities is constructed stereoselectively.

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Functional-Group-Directed Regiodivergent (3 + 2) Annulations of Electronically Distinct 1,3-Dienes and 2-Formyl Arylboronic Acids

Liang,

Zhang,

Chen

et al. 2024

Org. Lett.

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Palladium-Catalyzed Ligand-Controlled Switchable Hetero-(5 + 3)/Enantioselective [2σ+2σ] Cycloadditions of Bicyclobutanes with Vinyl Oxiranes

Zhou,

Xiao,

et al. 2024

J. Am. Chem. Soc.

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For nearly 60 years, significant research efforts have been focused on developing strategies for the cycloaddition of bicyclobutanes (BCBs). However, higher-order cycloaddition and catalytic asymmetric cycloaddition of BCBs have been long-standing formidable challenges. Here, we report Pd-catalyzed ligand-controlled, tunable cycloadditions for the divergent synthesis of bridged bicyclic frameworks. The dppb ligand facilitates the formal (5+3) cycloaddition of BCBs and vinyl oxiranes, yielding valuable eight-membered ethers with bridged bicyclic scaffolds in 100% regioselectivity. The Cy-DPEphos ligand promotes selective hetero-[2σ+2σ] cycloadditions to access pharmacologically important 2-oxabicyclo[3.1.1]heptane (O-BCHeps). Furthermore, the corresponding catalytic asymmetric synthesis of O-BCHeps with 94–99% ee has been achieved using chiral (S)-DTBM-Segphos, representing the first catalytic asymmetric cross-dimerization of two strained rings. The obtained O-BCHeps are promising bioisosteres for ortho-substituted benzenes.

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Recent advances in ligand-enabled palladium-catalyzed divergent synthesis

Abstract: In this review, recent advances in ligand-enabled palladium-catalyzed divergent synthesis are reported.

Cited by 2 publications

References 137 publications

Functional-Group-Directed Regiodivergent (3 + 2) Annulations of Electronically Distinct 1,3-Dienes and 2-Formyl Arylboronic Acids

Functional-Group-Directed Regiodivergent (3 + 2) Annulations of Electronically Distinct 1,3-Dienes and 2-Formyl Arylboronic Acids

Palladium-Catalyzed Ligand-Controlled Switchable Hetero-(5 + 3)/Enantioselective [2σ+2σ] Cycloadditions of Bicyclobutanes with Vinyl Oxiranes

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