Mechanochemical Aliphatic Iodination (and Bromination) by Cascaded Cyclization

Abstract

Aliphatic iodination via mechanochemistry is a mammoth challenge due to the high polarizability and weak electrophilicity of iodonium cation (I + ), and low bond dissociation energy of carbon iodine bond. Herein, the synthesis is demonstrated of oxazoline derivatives from Nallyl benzamides via mechanochemical cascaded cyclization and halogenation using N-iodo-and N-bromosuccinimides, respectively, as bifunctional reagents.

Toward a General Protocol for Catalytic Oxidative Transformations Using Electrochemically Generated Hypervalent Iodine Species

“…Ions were generated by electrospray ionization (ESI), and only the mass ions are reported. Spectral data for previously reported compounds are in good agreement with literature: 1a , 56 1b , 50 1c , 56 1d , 56 1e , 56 1f , 57 1i , 58 1j , 59 1k , 60 1l , 60 1m , 60 1n , 61 1o , 58 1p , 58 1s , 62 1u , 58 1v , 63 1w , 51 1x , 51 1z , 50 4a , 22 4b , 22 4c , 64 4d , 65 4e , 64 4g . 22 Ketones 3a–g were all purchased from Fluorochem and were used as received.…”