Tandem C-O and C-N bonds Formation Through O-Arylation and [3,3]-Rearrangement by Diaryliodonium Sal

来源 :中国化学会全国第十二届有机合成化学学术研讨会 | 被引量 : 0次 | 上传用户:glamour269
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  Metal-free O-arylation and [3,3]-rearrangement have been showed as an efficient strategy to construct new C-O and C-C bond in one-pot reaction.Very recently,Kürti and Olofsson independently developed metal-free O-arylation of oximes with diaryliodonium salts as accesses to O-arylhydroxylamines and synthesis of benzofuran scaffolds via formation of C-O and C-C bonds.During the studies of N-O bond rearrangement in our group,N-aryl benzo[1,2,3]triazin-4(1H)-one derivatives could be prepared in good yields from N-hydroxy benzo[1,2,3]triazin-4(3H)-one with diaryliodonium salts by formation of C-O and C-N bonds in one-pot reaction.The reaction was tolerated a variety of sensitive functional groups such as iodine,nitro,ester,and aldehyde groups.A rational mechanism was proposed based on the experimental results and the reaction was easily up to gram scale.
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