Solvent- and catalyst-dependent palladium-catalyzed switchable chemodivergent cascade cyclizations of trimethylenemethanes with ortho-formyl cinnamates

文献情報

出版日 2023-11-30

DOI 10.1039/D3QO01525D

インパクトファクター 5.281

著者

Shuyuan Liang, Liangjian Tang, Ying Chen, Xueqiu Huang, Xueqin Wei

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要旨

Chemodivergent synthetic methodologies enable the efficient generation of structural diversity via simple transformations. Here we develop the palladium-catalyzed chemodivergent cascade cyclization of trimethylenemethane (TMM) with dielectrophilic ortho-formyl cinnamates by effectively regulating solvents and H-bond donor (HBD) co-catalysts. Hexahydrocyclopenta[a]inden-8-ols are obtained through a CC-selective [3 + 2] cycloaddition/aldol process catalyzed by Pd(PPh3)4 in DME, whereas aryl-substituted cyclopentenes are exclusively afforded by tuning the substituents of dielectrophiles. Furthermore, a CO-selective [3 + 2]/Michael process affords tetrahydro-2H-indeno[1,2-b]furan architectures enabled by palladium/urea cooperative catalysis.

掲載誌

Organic Chemistry Frontiers

CiteScore: 7.8

自己引用率: 8.7%

年間論文数: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

Solvent- and catalyst-dependent palladium-catalyzed switchable chemodivergent cascade cyclizations of trimethylenemethanes with ortho-formyl cinnamates

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