Work

O -Vinylhydroxylamines for De Novo Pyrrole Synthesis

Year: 2026

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide Regioselective access to electron-deficient and highly substituted pyrroles from simple building blocks remains challenging. Here we show that O -vinylhydroxylamines enable the de novo construction of pyrroles through an aza-Michael/oxaza-Cope [3,3]-sigmatropic rearrangement/aromatization cascade with activated alkynes. This one-pot transformation proceeds rapidly at room temperature using catalytic amounts of a mild organic base and furnishes dihydropyrrole hemiaminal intermediates that can be directly converted to pyrroles or selectively functionalized. The method accommodates a broad range of O -vinylhydroxylamines and activated alkyne partners and enables access to substitution patterns that previously required harsh conditions or hazardous acetylene-based methods. These results establish O -vinylhydroxylamines as versatile building blocks for the synthesis of highly functionalized pyrroles.

Source: Journal of the American Chemical Society

DOI: 10.1021/jacs.6c06697

Authors: Charlotte Randolph, Oleksandr Buravov, Zachary Grimm, Pavel K. Mykhailiuk, László Kürti

Institutions: Rice University, State Scientific Institution “Institute for Single Crystals” of National Academy of Sciences of Ukraine, Enamine (Ukraine), Taras Shevchenko National University of Kyiv

Language: English

Topic: Synthesis and Characterization of Pyrroles

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500