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Issue 12, 2011
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Novel [4 + 2] cycloaddition reactions of alkyne and enyne key-units: Direct access to bicyclic aromatic and heteroaromatic products. A theoretical mechanistic study

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Abstract

A new efficient approach was developed for the synthesis of aromatic and heteroaromatic compounds based on [4 + 2] cycloaddition of unsubstituted and heteroatom-substituted alkyne and enyne units. The developed approach provides a practical Green chemical route to several types of important bicyclic products (indane, cyclopentapyridines, indole, isoindole, indolizine, isophosphindole, benzofuran, benzothiophene, benzoselenophene and corresponding dihydro derivatives) starting from simple linear compounds. The mechanism of the reactions was revealed by theoretical calculations using different methods, including CCSD(T) and MP4(SDTQ) for energy calculations and B3LYP, M052X, B3PW91, BLYP and MP2 levels for evaluation of molecular structures.

Graphical abstract: Novel [4 + 2] cycloaddition reactions of alkyne and enyne key-units: Direct access to bicyclic aromatic and heteroaromatic products. A theoretical mechanistic study

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Publication details

The article was received on 21 Jun 2011, accepted on 06 Sep 2011 and first published on 15 Sep 2011


Article type: Edge Article
DOI: 10.1039/C1SC00380A
Citation: Chem. Sci., 2011,2, 2332-2341
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    Novel [4 + 2] cycloaddition reactions of alkyne and enyne key-units: Direct access to bicyclic aromatic and heteroaromatic products. A theoretical mechanistic study

    V. P. Ananikov and E. G. Gordeev, Chem. Sci., 2011, 2, 2332
    DOI: 10.1039/C1SC00380A

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