The domino hexadehydro-Diels-Alder reaction transforms polyynes to benzynes to naphthynes to anthracynes to tetracynes (and beyond?)

Nature Chemistry
Xiao Xiao, Thomas R Hoye

Abstract

Polyacenes are organic compounds that have multiple, fused, aromatic rings. These highly conjugated molecules often have interesting photonic and/or electronic properties that afford them the potential for application in a host of organoelectronic devices such as sensors, light-emitting diodes, photovoltaic devices and field-effect transistors. Here, we show the development and use of the domino hexadehydro-Diels-Alder reaction to synthesize structurally diverse polyacenes from acyclic polyyne precursors. The key event in these transformations is the successive reaction of multiple 1,3-butadiyne units with a series of in-situ-generated, diynophilic arynes. The polyyne substrates were designed to allow for rapid engagement of each progressively larger aryne following the initiating (and ratelimiting) production of the first reactive intermediate-the benzyne. We show that aryne-trapping reactions are broad in scope and that these cascade or domino processes can be quite efficient.

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Citations

Apr 28, 2020·Chemistry : a European Journal·Aneta KurpanikStanisław Krompiec
Nov 21, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Aneta KurpanikStanisław Krompiec
Apr 23, 2021·Organic Letters·Sahil Arora, Thomas R Hoye
May 1, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Anton BudeevMikhail Krasavin
Mar 30, 2021·Chemistry : a European Journal·Mingxuan FanQichun Zhang
Jun 4, 2021·Angewandte Chemie·Melissa RamirezNeil K Garg
Jun 12, 2019·Journal of the American Chemical Society·Xiao Xiao, Thomas R Hoye
Mar 6, 2019·The Journal of Organic Chemistry·Karthik DevarajLukasz T Pilarski
May 22, 2020·Organic Letters·Matthew S McVeighNeil K Garg
Jun 30, 2019·Organic Letters·Yu NakamuraTakamitsu Hosoya
Oct 5, 2018·Journal of the American Chemical Society·Dachuan QiuYang Li
Feb 7, 2020·The Journal of Organic Chemistry·Tsuneyuki KobayashiSuguru Yoshida
Jan 28, 2020·Accounts of Chemical Research·Jia HeYang Li
Sep 24, 2021·Chemistry : a European Journal·Mikhail FeofanovKonstantin Amsharov

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Methods Mentioned

BETA
X-ray
NMR

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