Bicyclo[2.1.1]hexanes by Visible Light-Driven Intramolecular Crossed [2 + 2] Photocycloadditions

Thomas Rigotti; Thorsten Bach

doi:10.1021/acs.orglett.2c03606

Bicyclo[2.1.1]hexanes by Visible Light-Driven Intramolecular Crossed [2 + 2] Photocycloadditions

Org Lett. 2022 Dec 9;24(48):8821-8825. doi: 10.1021/acs.orglett.2c03606. Epub 2022 Nov 22.

Authors

Thomas Rigotti¹, Thorsten Bach¹

Affiliation

¹ Technical University of Munich, School of Natural Sciences, Department of Chemistry and Catalysis Research Center, Lichtenbergstrasse 4, 85747Garching, Germany.

PMID: 36414533
DOI: 10.1021/acs.orglett.2c03606

Abstract

Bicyclo[2.1.1]hexanes have become increasingly popular building blocks in medicinal chemistry as bridged scaffolds that provide unexplored chemical space. We herein report a visible light-driven approach to these compounds that relies on an intramolecular crossed [2 + 2] photocycloaddition of styrene derivatives enabled by triplet energy transfer. Bicyclo[2.1.1]hexanes were obtained in good to high yields (19 examples, 61%-quantitative yield) and allowed for further functionalizations by consecutive reactions, thereby opening different pathways to decorate the aliphatic core structure.