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作为亲核试剂的烯酰胺和烯磺酰胺:通过铂(II)催化加成/Friedel-Crafts 途径形成复杂的环体系。

Enamides and enesulfonamides as nucleophiles: formation of complex ring systems through a platinum(II)-catalyzed addition/Friedel-Crafts pathway.

机构信息

Department of Chemistry, 2036 Main Mall, University of British Columbia, Vancouver, BC, Canada V6T 1Z1.

出版信息

J Org Chem. 2009 Sep 18;74(18):6929-35. doi: 10.1021/jo901512m.

DOI:10.1021/jo901512m
PMID:19689099
Abstract

Cyclic enamine derivatives (enesulfonamides and enamides) tethered to an 1-arylalkynyl fragment undergo a platinum(II)-catalyzed tandem alkyne addition/Friedel-Crafts ring closure to form nitrogen-containing polycyclic structures. Regioselectivity in the initial addition of the enesulfonamide or enamide nucleophile to the platinum(II)-alkyne complex is important. Electron-rich arenes and heterocycles led to the formation of products resulting from an initial 6-endo cyclization. Twenty-three examples of this process are presented.

摘要

含 1-芳基炔基片段的环烯胺衍生物(烯磺酰胺和烯酰胺)经历铂(II)催化的串联炔加成/Friedel-Crafts 环化反应,形成含氮多环结构。在烯磺酰胺或烯酰胺亲核试剂与铂(II)-炔络合物的初始加成中,区域选择性很重要。富电子芳环和杂环导致形成初始 6-endo 环化反应生成的产物。本文提供了 23 个这种过程的实例。

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