Hexadehydro-diels-alder reaction: Benzyne generation via cycloisomerization of tethered triynes

Lucas L. Fluegel, Thomas R. Hoye

Research output: Contribution to journalReview articlepeer-review

103 Scopus citations


The hexadehydro-Diels-Alder (HDDA) reaction is the thermal cyclization of an alkyne and a 1,3-diyne to generate a benzyne intermediate. This is then rapidly trapped, in situ, by a variety of species to yield highly functionalized benzenoid products. In contrast to nearly all other methods of aryne generation, no other reagents are required to produce an HDDA benzyne. The versatile and customizable nature of the process has attracted much attention due not only to its synthetic potential but also because of the fundamental mechanistic insights the studies often afford. The authors have attempted to provide here a comprehensive compilation of publications appearing by mid-2020 that describe experimental results of HDDA reactions.

Original languageEnglish (US)
Pages (from-to)2413-2444
Number of pages32
JournalChemical Reviews
Issue number4
StatePublished - Feb 24 2021

Bibliographical note

Funding Information:
Aspects of this research are supported in T.R.H.’s laboratory by grants from the Institute of General Medical Sciences of the United States Department of Health and Human Services (R35 GM127097) and the United States National Science Foundation (CHE-1665389).

Publisher Copyright:
© 2021 American Chemical Society


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