Rhenium- and manganese-catalyzed synthesis of aromatic compounds from 1,3-dicarbonyl compounds and alkynes

Yoichiro Kuninobu, Mitsumi Nishi, Atsushi Kawata, Hisatsugu Takata, Yumi Hanatani, S. Salprima Yudha, Aya Iwai, Kazuhiko Takai

Research output: Contribution to journalArticle

28 Citations (Scopus)

Abstract

(Chemical Equation Presented) We have succeeded in the development of three approaches to the synthesis of aromatic compounds from 1,3-dicarbonyl compounds and alkynes. The first approach is a manganese-catalyzed [2+2+2] cycloaddition between 1,3-dicarbonyl compounds, which have no substituents at the active methylene moiety, and terminal alkynes. This reaction proceeds with high regioselectivity when aryl acetylenes are employed as the alkyne component. The second approach is a rhenium- or manganese-catalyzed formal [2+1+2+1] cycloaddition between β-keto esters and two kinds of alkynes. In this reaction, the aromatic compounds are obtained by the following reaction sequence: (1) insertion of the first alkyne into a carbon-carbon single bond of a β-keto ester, (2) formation of 2-pyranones via intramolecular cyclization with the elimination of ethanol, and (3) Diels-Alder reaction between the formed 2-pyranone and the second alkyne. This reaction provides multisubstituted aromatic compounds in a regioselective manner. The third approach is a rheniumcatalyzed formal [2+2+1+1] cycloaddition reaction from two 1,3-diketones and one alkyne. In this reaction, the aromatic skeleton is constructed from three carbons of the first 1,3-diketone, two carbons of the alkyne, and one carbon of the second 1,3-diketone.

Original languageEnglish
Pages (from-to)334-341
Number of pages8
JournalJournal of Organic Chemistry
Volume75
Issue number2
DOIs
Publication statusPublished - Jan 15 2010
Externally publishedYes

    Fingerprint

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this