钯催化苯乙酰胺与 1,3-二烯的[5 + 2]杂环加成反应构建多巴胺能 3-苯并氮杂卓。
Palladium-Catalyzed [5 + 2] Heteroannulation of Phenethylamides with 1,3-Dienes to Dopaminergic 3-Benzazepines.
机构信息
Centro Singular de Investigación en Química Biolóxica e Materiais Moleculares (CiQUS), Departamento de Química Orgánica, Universidade de Santiago de Compostela, 15782 Santiago de Compostela, Spain.
出版信息
Org Lett. 2020 May 1;22(9):3591-3595. doi: 10.1021/acs.orglett.0c01053. Epub 2020 Apr 19.
Phenethyltriflamides react with 1,3-dienes upon treatment with a catalytic amount of Pd(OAc) and Cu(OAc)/O as oxidant to afford chemo-, regio- and diastereoselectively 2,3,4,5-tetrahydro-1-benzo[]azepines (3-benzazepine derivatives) in good to excellent yields. A DFT study of the [5 + 2] heteroannulation suggests a mechanistic pathway starting with formation of the six-membered palladacycle -PdXL via a CMD process followed by η coordination and insertion of the 1,3-diene unit in a diastereoselective manner.
苯乙三氟酰胺在催化量的 Pd(OAc) 和 Cu(OAc)/O 作用下与 1,3-二烯反应，以良好到优异的收率选择性地得到化学、区域和立体选择性的 2,3,4,5-四氢-1-苯并[ ]氮杂卓（3-苯并氮杂卓衍生物）。通过 DFT 研究[5 + 2]杂环加成反应，提出了一种可能的反应机理，该机理首先通过 CMD 过程形成六元钯环-PdXL，然后 η 配位并以立体选择性的方式插入 1,3-二烯单元。
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