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September 10, 2025

HFIP-Mediated Ring Opening of Bicyclo1.1.0butanes with Hydroperoxides for Diastereoselective Access to Peroxycyclobutanes

PGPriyanshu GuptaMicrosoft Research (India)PRPolly RoyUniversity of South Florida ABAkkattu T. BijuIndian Institute of Science Bangalore

Key Points

Diastereoselective synthesis of peroxycyclobutanes occurred under mild conditions with broad substrate scope.
Density functional theory studies provide vital insights into the reaction mechanism and stereochemical outcomes.
HFIP proved essential for activating bicyclo[1.1.0]butanes to facilitate efficient nucleophilic addition.
The approach offers a transition-metal-free pathway, enhancing reaction simplicity and scope.

Abstract

A transition-metal-free ring opening of bicyclo1.1.0butanes (BCBs) using hydroperoxides as nucleophiles in hexafluoroisopropanol (HFIP) resulting in the diastereoselective synthesis of peroxycyclobutanes under mild conditions with a broad scope is demonstrated. Preliminary mechanistic experiments, including density functional theory studies, provide insight into the mechanism and stereochemical outcome of the reaction, thus underscoring the unique role of HFIP in activating BCB for facile nucleophilic addition.

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