DDQ/TFA: an Efficient Nonmetallic Reagent System for the Oxidative Coupling to Construct Phenanthrene Rings

doi:10.1007/s40242-014-3561-9

Abstract

Abstract:

A mild synthetic method of a series of phenanthrenes with different substituents on the phenanthrene ring is described. The method involves intramolecular oxidative coupling with 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ)/trifluoroacetic acid(TFA) as oxidant to produce phenanthrenes in high yields and is fit for large-scale preparation. Furthermore, DDQ can be regenerated by a simple oxidation. The present approach solves a key step for the synthesis of polycyclic structures related to an alkaloid tylophorine.

Key words: Intramolecular oxidative coupling, 2,3-Dichloro-5,6-dicyanobenzoquinone(DDQ), 1,2-Diarylethylene, Phenanthrene ring, Alkaloid

LI Ling, HU Yanna, WANG Kailiang, WANG Qingmin. DDQ/TFA: an Efficient Nonmetallic Reagent System for the Oxidative Coupling to Construct Phenanthrene Rings[J]. Chemical Research in Chinese Universities, 2014, 30(4): 619-623.

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