BF3 center dot OEt2-mediated [1,2]-aryl shift: Synthesis of functionalized alpha-arylnitriles via the bromination/cyanation/deformylation of substituted deoxybenzoin

摘要

A new sequential, tandem synthesis of functionalized alpha-arylnitriles via the brominationicyanationi deformylation of substituted deoxybenzoin has developed. CuBr2-promoted bromination of substituted deoxybenzoins gives 2-bromo-2-arylacetophenne 3. The cyanation of 3 with sodium cyanide (NaCN) generates epoxynitrile. Then, a treatment of epoxynitrile with BF-3OEt2 results in the formation of functionalized alpha-arylnitriles 4 via a 1,2-aryl shift. (C) 2017 Elsevier Ltd. All rights reserved.