铼催化通过碳-碳单键裂解合成多取代芳香族化合物。

Rhenium-catalyzed synthesis of multisubstituted aromatic compounds via C-C single-bond cleavage.

作者信息

Kuninobu Yoichiro, Takata Hisatsugu, Kawata Atsushi, Takai Kazuhiko

机构信息

Division of Chemistry and Biochemistry, Graduate School of Natural Science and Technology, Okayama University, Tsushima, Okayama, Japan.

出版信息

Org Lett. 2008 Jul 17;10(14):3133-5. doi: 10.1021/ol801226t. Epub 2008 Jun 19.

DOI:10.1021/ol801226t

PMID:18563904

Abstract

A reaction between a beta-keto ester and an acetylene in the presence of a rhenium complex, [ReBr(CO)3(thf)]2, as a catalyst, provided a 2-pyranone derivative in excellent yield via retro-aldol reaction (C-C single bond cleavage). By adding an acetylene-bearing ester group(s) after the formation of 2-pyranones, an aromatization reaction proceeded and multisubstituted aromatic compounds were obtained in good to excellent yields.

摘要

在铼配合物[ReBr(CO)₃(thf)]₂作为催化剂存在的情况下，β-酮酯与乙炔之间的反应通过逆羟醛反应（C-C单键断裂）以优异的产率提供了一种2-吡喃酮衍生物。在2-吡喃酮形成后加入含乙炔的酯基，芳构化反应进行，多取代芳香族化合物以良好至优异的产率得到。