Mechanochemical Preferential Bromination at the α‐Position of Activated Naphthalenes

This study focuses on the mechanochemical pathway for α-bromination of β-functionalized naphthalenes. This uses N-bromosuccinimide as a mild brominating precursor and highlights the tolerance and limitations of functional groups used. This applies on gram scale synthesis and production of various useful intermediates.

Abstract

This study is the exploration of a solvent-free, mechanochemically enabled sustainable pathway for rapid and preferential selective α-bromination of β-functionalized naphthalenes using N-bromosuccinimide. Gram-scale synthesis and diverse post-functionalizations demonstrate the versatility of the α-brominated β-functionalized naphthalenes in organic synthesis, pharmaceuticals, materials, and catalysis. This green and environment-benign approach, having E-factor of 0.5, offers high yields up to 98% within 30 minutes and highlights broad functional electron-donating groups (EDGs) along with limitations of electron-withdrawing groups (EWGs).

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