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Issue 5, 2017
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Methodology and applications of the hexadehydro-Diels–Alder (HDDA) reaction

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Abstract

The hexadehydro-Diels–Alder (HDDA) reaction between an alkyne and a 1,3-diyne has recently become a rapidly growing area in the field of aryne chemistry. Both concerted and stepwise mechanisms for HDDA are energetically and geometrically feasible. The formation of a reactive benzyne intermediate under thermal conditions has been coupled with a wide variety of intra- and intermolecular trapping reactions to access highly functionalised aromatic compounds. With this in mind, reagents can be tailored to generate compounds for desired applications such as the synthesis of bioactive molecules or optoelectronic materials. This review presents a comprehensive overview of the HDDA reaction to date.

Graphical abstract: Methodology and applications of the hexadehydro-Diels–Alder (HDDA) reaction

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Article information


Submitted
24 Jan 2017
Accepted
16 Mar 2017
First published
20 Mar 2017

Org. Chem. Front., 2017,4, 891-910
Article type
Review Article

Methodology and applications of the hexadehydro-Diels–Alder (HDDA) reaction

O. J. Diamond and T. B. Marder, Org. Chem. Front., 2017, 4, 891
DOI: 10.1039/C7QO00071E

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