Bicyclo2.2.1heptanes (BCHeps) are essential polycyclic compounds in many natural products and pharmaceutical molecules. Efficient synthetic strategies for BCHeps and their derivatives are desirable and challenging. In this work, bicyclo2.1.0pentanes (BCPs) have been strategically employed as building blocks for the development of a 2π + 2σ cycloaddition reaction with alkenes. The key to success is using a pyridine-assisted boronyl radical catalysis approach. This provides a modular and atom-economical method, using simple and inexpensive catalysts, for efficient synthesis of BCHeps. The substrate scope has been explored. A possible reaction mechanism has been proposed, and the synthetic utility has been demonstrated by downstream transformations.
Perveen et al. (Mon,) studied this question.