Work

1 H -Isoindolynes: Arynes Accessible by a One-Pot, Ambient Temperature, Three-Component Cascade

Year: 2026

Type: article

Abstract: We describe here a new type of aryne: 1 H -isoindolynes. These can be accessed by variants of a process in which a primary propargylic diynol, a propargylic aminodiyne, and an aryne-trapping agent are treated with an oxidizing agent capable of producing, in situ, a 2,4-diynal. This mixture undergoes a room temperature cascade of events involving imine condensation, imine E -to- Z isomerization, hexadehydro-Diels−Alder cycloisomerization, and a final aryne-trapping reaction. This convergent strategy gives isoindolyne adducts in good to excellent yields. Insights into subtle aspects of the mechanism were gained by examining the reaction by 1 H NMR spectroscopy, through control reactions involving isolable iminotriynes, and using density functional theory calculations.

Source: The Journal of Organic Chemistry

DOI: 10.1021/acs.joc.5c03027

Authors: Niklas Kraemer, Thomas R. Hoye

Institution: University of Minnesota

Language: English

Topic: Cyclization and Aryne Chemistry

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: National Social Science Fund of China, National Institute of General Medical Sciences

Awards: G506717095, G6346998295