Palladium-Catalyzed Intermolecular Acylative Heck Reactions with Imides as Acyl Electrophiles
Palladium-Catalyzed Intermolecular Acylative Heck Reactions with Imides as Acyl Electrophiles
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钯催化酰亚胺作为酰基亲电子试剂的分子间酰化 Heck 反应
DOI：
10.1021/acs.joc.1c00087
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发表时间：
2021
期刊：
影响因子：
--
通讯作者：
Stanley, Levi M.
中科院分区：
文献类型：
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作者：
Kadam, Abhishek A.;Metz, Tanner L.;David, Colton M.;Koeritz, Mason T.;Stanley, Levi M.
我们公开了使用酰亚胺作为酰基亲电试剂的钯催化的分子间酰化Heck反应。[Pd（allyl）Cl] 2和DPEphos生成的催化剂在银磷酸盐存在下促进了N-苯甲酰基戊二酰亚胺与异戊烯的反应。酰化Heck反应包括一系列N-苯甲酰基戊二酰亚胺亲电试剂，这些试剂含有供电子、卤代和吸电子取代基，以中等至高产率（25-82%）生成α，β-不饱和酮。双环α，β-不饱和酮通过热杂-Diels-桤木反应很容易转化为多环结构，该反应通过α，β-不饱和酮的二聚反应发生。
We disclose palladium-catalyzed, intermolecular, acylative Heck reactions that use imides as acyl electrophiles. The catalyst generated from [Pd(allyl)Cl]2and DPEphos promotes the reaction betweenN-benzoylglutarimides and norbornene in the presence of silver phosphate. The acylative Heck reaction encompasses an array ofN-benzoylglutarimide electrophiles that contain electron-donating, halogenated, and electron-withdrawing substituents to generate α,β-unsaturated ketones in moderate to high yields (25–82%). The bicylic α,β-unsaturated ketones are readily transformed into polycyclic architectures via thermal hetero-Diels–Alder reactions that occur by the dimerization of the α,β-unsaturated ketones.