Diazomethyl-λ³-iodane meets aryne: Dipolar cycloaddition and C-to-N iodane shift leading to indazolyl-λ³-iodanes

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

Published: Jan. 1, 2025

Diazomethyl-λ 3 -iodanes have recently emerged as carbyne equivalents in organic synthesis, enabling the construction of multi-substituted carbon centers through strategic sequential activation diazo and iodane functional groups. Distinct from...

Language: Английский

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

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

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Recent advances in haloarene synthesis by aryne reactions

Tetrahedron Chem, Journal Year: 2025, Volume and Issue: unknown, P. 100136 - 100136

Published: May 1, 2025

Language: Английский

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