Catalyst-free selenylation/semipinacol rearrangement cascades of alkenyl cyclobutanols: synthesis of β-selenylated cyclopentanones

Abstract

A simple and practical strategy to access β-selenated cyclic ketone derivatives through the catalyst-free selenylation and semipinacol rearrangement sequence of 1-(1-arylvinyl)cyclobutanols was developed. This reaction employs the easily accessible and shelf-stable benzeneselenyl bromide as an electrophilic selenium source, and the reaction has advantages of mild reaction conditions and broad substrate scope.

Graphical Abstract

Keywords:

• 1,2-Alkyl migration
• 1-(1-arylvinyl)cyclobutanols
• benzeneselenyl bromide
• selenylation
• semipinacol rearrangement

Additional information

Funding

This research was supported by Soonchunhyang University Research Fund and Basic Science Research Program through the National Research Foundation of Korea (NRF-2016R1D1A1B03933723).