Hexadehydro-Diels–Alder reaction: Benzyne generation via cycloisomerization of tethered triynes

LL Fluegel, TR Hoye - Chemical reviews, 2021 - ACS Publications
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 …

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

OJ Diamond, TB Marder - Organic Chemistry Frontiers, 2017 - pubs.rsc.org
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 …

The renaissance and bright future of synthetic aryne chemistry

S Yoshida, T Hosoya - Chemistry Letters, 2015 - academic.oup.com
Recent developments in aryne chemistry are reviewed with a particular focus on synthetic
methods. This includes an overview of the precursors of arynes and their activators; the …

Aryne 1, 2, 3-trifunctionalization with aryl allyl sulfoxides

Y Li, D Qiu, R Gu, J Wang, J Shi… - Journal of the American …, 2016 - ACS Publications
An aryne 1, 2, 3-trisubstitution with aryl allyl sulfoxides is accomplished, featuring an
incorporation of C–S, C–O, and C–C bonds on the consecutive positions of a benzene ring …

Reactions of hexadehydro-Diels–Alder benzynes with structurally complex multifunctional natural products

SP Ross, TR Hoye - Nature chemistry, 2017 - nature.com
An important question in organic chemistry concerns the extent to which benzynes—one of
the classical reactive intermediates in organic chemistry—can react in discriminating fashion …

Reactions of HDDA-derived benzynes with sulfides: Mechanism, modes, and three-component reactions

J Chen, V Palani, TR Hoye - Journal of the American Chemical …, 2016 - ACS Publications
We report here reactions of alkyl sulfides with benzynes thermally generated by the
hexadehydro-Diels–Alder (HDDA) cycloisomerization. The initially produced 1, 3-betaine (o …

Metal-free homo-/cross-anion–cation coupling of cyclic diaryl λ 3-bromanes

Y Wang, YN Tian, S Ren, R Zhu, B Huang… - Organic Chemistry …, 2023 - pubs.rsc.org
The homo anion–cation coupling of cyclic diaryl λ3-bromanes/diarylbrominiums, which was
not reported in previous reports, has been disclosed for the first time. The competition …

Photochemical hexadehydro-Diels–Alder reaction

F Xu, X Xiao, TR Hoye - Journal of the American Chemical Society, 2017 - ACS Publications
We demonstrate that the hexadehydro-Diels–Alder (HDDA) cycloisomerization reaction to
produce reactive benzyne derivatives can be initiated photochemically. As with the thermal …

[HTML][HTML] Intramolecular hydride transfer onto arynes: redox-neutral and transition metal-free C (sp 3)–H functionalization of amines

FIM Idiris, CE Majesté, GB Craven, CR Jones - Chemical Science, 2018 - pubs.rsc.org
Transition metal-free intramolecular hydride transfer onto arynes is reported for the first time.
This unique transformation is utilized in redox-neutral intermolecular α-functionalization …

The pentadehydro-diels–alder reaction

T Wang, RR Naredla, SK Thompson, TR Hoye - Nature, 2016 - nature.com
Abstract In the classic Diels–Alder [4+ 2] cycloaddition reaction, the overall degree of
unsaturation (or oxidation state) of the 4π (diene) and 2π (dienophile) pairs of reactants …