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苯衍生物的多样性合成:Brønsted 酸催化和碘促进的 5,2-烯炔-1-酮串联环化反应。

Divergent synthesis of benzene derivatives: Brønsted acid catalyzed and iodine-promoted tandem cyclization of 5,2-enyn-1-ones.

机构信息

State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, People's Republic of China.

出版信息

J Org Chem. 2012 Oct 19;77(20):9029-37. doi: 10.1021/jo301567p. Epub 2012 Sep 27.

Abstract

Highly substituted benzene derivatives, including alkoxy-, iodoalkoxy-, and diiodo-substituted benzenes, can be selectively synthesized via Brønsted acid catalyzed and iodine-promoted tandem carbocyclization respectively. This reaction involved a direct process for C-C bond formation from 5,2-enyn-1-ones, and different reaction systems (Brønsted acids/electrophiles with solvents) afforded different substituted benzenes. Furthermore, the halogenated moiety and alkoxy group can be readily introduced into the benzene in a position which has not been easily obtained previously.

摘要

高度取代的苯衍生物,包括烷氧基、碘代烷氧基和二碘代取代的苯,可以分别通过布朗斯特酸催化和碘促进的串联碳环化反应选择性合成。该反应涉及一种从 5,2-烯炔-1-酮直接形成 C-C 键的过程,不同的反应体系(布朗斯特酸/亲电试剂与溶剂)得到不同取代的苯。此外,卤代部分和烷氧基可以很容易地引入苯环中,而这些位置以前很难获得。

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