An enantioselective insertion reaction of silver carbenes generated from donor-acceptor-substituted diazo compounds into the OÀHb ond of phenols wasd eveloped. Ah omobinuclear silver complexw ith ac hiral phosphorous ligand was created in situ from AgNTf 2 and (S)-XylylBINAP( in a2 :1 mole ratio). Detailed mechanistic studies using combined experimental and computational techniquesr evealed that one silver atom centero ft he catalyst formsasilver carbene and another one works as a Lewis acid fort he nucleophilic addition of ap henol.T wo counter-anions,t wo water molecules,a nd two silver atoms cooperatively mediate the subsequent protonation event to lower the activation energy and control enantioselectivity,a ffording an array of valuable a-aryl-a-aryloxy esters. Figure 1. Bioactive and usefulc ompoundspossessing a-aryl-a-aryloxy-carbonyl group and their derivatives.Scheme1.Reactions of naphthols and phenols with various metal-carbenes.[a] Dr.
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