Highly efficient and air-tolerant calcium-based Birch reduction using mechanochemistry

Abstract In this study, we report a mechanochemical protocol for highly efficient and air-tolerant calcium-based Birch reduction. The developed mechanochemical approach allows the use of readily available calcium metal as a safer-to-handle reductant for Birch reduction of various aromatic compounds. The reaction was rapid and the desired dearomatization products were obtained in good yields within 15 min at ambient temperature. Notably, all synthetic operations can be performed under ambient conditions without a complicated reaction setup involving inert gases. The feasibility of the gram-scale synthesis was demonstrated, further highlighting the practical utility of this protocol.