Hexadehydro Diels–Alder/Alkynyliodanation Cascade: A Highly Regioselective Entry to Polycyclic Aromatics DOI Creative Commons

Shunya Morohashi,

Liejin Zhou, Kazuya Kanemoto

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: April 15, 2025

We report here a cascade process integrating the hexadehydro Diels-Alder (HDDA) reaction with alkynyliodanation, enabling efficient synthesis of highly substituted aryl-λ3-iodanes. Heating mixture tetrayne and an alkynylbenziodoxole induces regioselective insertion tetrayne-derived aryne into alkynyl-iodine(III) bond, yielding 1,4-dialkynyl-2-iodanyl-3-aryl(or alkyl)benzene derivative. The unique regiochemistry facilitates subsequent π-extension, allowing divergent access to polyaromatic frameworks, such as helicenes cyclopenta[cd]pyrenes, underscoring utility carboiodanation in complex aromatic synthesis.

Language: Английский

Aryne Generation from o-Triazenylarylboronic Acids Induced by 1,2-Diols and 4-Nitrophenol DOI
Motoki Ito,

Hiroki Yomo,

Kazuhiro Higuchi

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 30, 2025

Arynes are important synthetic intermediates that usually generated under alkaline conditions. We developed a method for generating arynes using two hydroxy compounds as activators. o-Triazenylarylboronic acids generate (hetero)arynes when activated by combination of ethylene glycol, pinacol, and p-nitrophenol; these then react with range arynophiles slightly acidic conditions complement the conventional basic unique chemoselectivities observed even in presence excess compounds.

Language: Английский

Citations

0
Benzyne Platform: A Strategic Approach to Developing Novel Intramolecular Reactions DOI
Hiroshi Takikawa

Journal of Synthetic Organic Chemistry Japan, Journal Year: 2025, Volume and Issue: 83(2), P. 131 - 141

Published: Feb. 1, 2025

Language: Английский

Citations

0
Iodonium(III) Ylide: An Iodoalkylation Reagent with Aryne DOI
Weigang Xu, Pengfei Li,

Yuerong Li

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 5, 2025

A tandem Hexadehydro-Diels–Alder (HDDA)/[2 + 2] cycloaddition/aryl migration reaction of iodonium ylide with tetrayne is described, in which served as a unique double bond and reacted aryne to form four-membered iodonium(III) cycle, then converted iodoarene after aryl group from iodine adjacent carbon. This strategy allows the efficient construction fully substituted compounds.

Language: Английский

Citations

0
Access to arynes from arenes via net dehydrogenation: scope, synthetic applications and mechanistic analysis DOI Creative Commons
Riley A. Roberts,

Bryan E. Metze,

Nicole Javaly

et al.

Chemical Science, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Arynes are versatile intermediates for organic synthesis and now they can be accessed from arenes in one or two-pot sequences via aryl thianthrenium ( situ ) iodonium (isolated) intermediates, respectively.

Language: Английский

Citations

0
Precise synthesis of ortho-deuterated aromatic derivatives: an arylthianthrenium salt-based platform approach DOI

Yunhao Guan,

Peng Xia, Rong Fan

et al.

Chinese Chemical Letters, Journal Year: 2025, Volume and Issue: unknown, P. 111132 - 111132

Published: March 1, 2025

Language: Английский

Citations

0
Cyclic Diphenylchloronium-Salt-Triggered Coupling of Sulfides with Nucleophiles: Modular Assembly of Pharmaceuticals DOI

Bangxiong Kang,

Wei Li, Huanfeng Jiang

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: April 2, 2025

We report a novel coupling strategy enabled by cyclic diphenylchloronium salt that facilitates reactions between sulfides and diverse nucleophiles, including oxygen- nitrogen-based species. The methodology efficiently produces structurally varied valuable compounds, carbamates, carboxylic esters, aryl ethers, alkylated amines, under mild, operationally simple conditions. protocol's synthetic utility was highlighted through modular preparation of five important drugs structural analogues, demonstrating significant potential for drug discovery applications.

Language: Английский

Citations

0
Hexadehydro Diels–Alder/Alkynyliodanation Cascade: A Highly Regioselective Entry to Polycyclic Aromatics DOI Creative Commons

Shunya Morohashi,

Liejin Zhou, Kazuya Kanemoto

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: April 15, 2025

We report here a cascade process integrating the hexadehydro Diels-Alder (HDDA) reaction with alkynyliodanation, enabling efficient synthesis of highly substituted aryl-λ3-iodanes. Heating mixture tetrayne and an alkynylbenziodoxole induces regioselective insertion tetrayne-derived aryne into alkynyl-iodine(III) bond, yielding 1,4-dialkynyl-2-iodanyl-3-aryl(or alkyl)benzene derivative. The unique regiochemistry facilitates subsequent π-extension, allowing divergent access to polyaromatic frameworks, such as helicenes cyclopenta[cd]pyrenes, underscoring utility carboiodanation in complex aromatic synthesis.

Language: Английский

Citations

0