Solvent- and catalyst-dependent palladium-catalyzed switchable chemodivergent cascade cyclizations of trimethylenemethanes with ortho-formyl cinnamates
Solvent- and catalyst-dependent palladium-catalyzed switchable chemodivergent cascade cyclizations of trimethylenemethanes with ortho-formyl cinnamates
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DOI：
10.1039/d3qo01525d
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发表时间：
2023-11-30
影响因子：
5.4
通讯作者：
Wei，Xueqin
中科院分区：
文献类型：
--
作者：
Liang，Shuyuan;Tang，Liangjian;Wei，Xueqin
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.
