Work

Light-enabled intramolecular [2 + 2] cycloaddition via photoactivation of simple alkenylboronic esters

Year: 2025

Type: article

Abstract: The photoactivation of organic molecules via energy transfer (EnT) catalysis is often limited to conjugated systems that have low-energy triplet excited states, with simple alkenes remaining an intractable challenge. The ability to address this limitation, using high energy sensitizers, would represent an attractive platform for future reaction design. Here, we disclose the photoactivation of simple alkenylboronic esters established using alkene scrambling as a rapid reaction probe to identify a suitable catalyst and boron motif. Cyclic voltammetry, UV-vis analysis, and control reactions support sensitization, enabling an intramolecular [2 + 2] cycloaddition to be realized accessing 3D bicyclic fragments containing a boron handle.

Source: Beilstein Journal of Organic Chemistry

DOI: 10.3762/bjoc.21.69

Authors: Lewis McGhie, Hannah M Kortman, Jenna Rumpf, Peter H Seeberger, John J Molloy

Institutions: Max Planck Society, Max Planck Institute of Colloids and Interfaces, Freie Universität Berlin

Language: English

Topic: Organoboron and organosilicon chemistry

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: diamond

Funders: Fonds der Chemischen Industrie, HORIZON EUROPE Framework Programme, HORIZON EUROPE European Research Council

Award: G6085128015