Combining palladium and ammonium halide catalysts for Morita-Baylis-Hillman carbonates of methyl vinyl ketone: from 1,4-carbodipoles to ion pairs.
Combining palladium and ammonium halide catalysts for Morita-Baylis-Hillman carbonates of methyl vinyl ketone: from 1,4-carbodipoles to ion pairs.
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DOI：
10.1039/d1sc03517g
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发表时间：
2021-09-01
期刊：
影响因子：
8.4
通讯作者：
Chen YC
中科院分区：
文献类型：
--
作者：
Yang Y;Zhu B;Zhu L;Jiang Y;Guo CL;Gu J;Ouyang Q;Du W;Chen YC
Here we report that Morita–Baylis–Hillman carbonates from diverse aldehydes and methyl vinyl ketones can be directly utilised as palladium-trimethylenemethane 1,4-carbodipole-type precursors, and both reactivity and enantioselectivity are finely regulated by adding a chiral ammonium halide as the ion-pair catalyst. The newly assembled intermediates, proposed to contain an electronically neutral π-allylpalladium halide complex and a reactive compact ion pair, efficiently undergo asymmetric [4 + 2] annulations with diverse activated alkenes or isatins, generally with high regio-, diastereo- and enantio-selectivity, and even switchable regiodivergent or diastereodivergent annulations can be well realised by tuning the substrate or catalyst assemblies. An array of control experiments, including UV/Vis absorption study and density functional theory calculations, are conducted to rationalise this new double activation mode combining a palladium complex and an ammonium halide as an ion-pair catalyst. A double activation catalytic system combining a palladium complex and an ammonium halide was developed to promote the asymmetric [4 + 2] annulations of Morita–Baylis–Hillman carbonates of methyl vinyl ketone.
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