An electrocatalytic 3,3-rearrangement/cyclization approach has been developed for the transformation of arylsubstituted propargylic aryl ethers to naphtho[1,2-b]furan-2-carbaldehyde and naphtho[2,1-b]furan-2-carbaldeh...An electrocatalytic 3,3-rearrangement/cyclization approach has been developed for the transformation of arylsubstituted propargylic aryl ethers to naphtho[1,2-b]furan-2-carbaldehyde and naphtho[2,1-b]furan-2-carbaldehyde derivatives.The reaction proceeded efficiently under mild conditions in the absence of metal-and chemicaloxidant,yielding the desired products with good substrate scope and functional group tolerance via a radical pathway.Furthermore,the control experiment revealed that the phenylselenyl-substituted secondary alcohol might be intermediate,and the ^(18)O labeling reaction indicated the oxygen source in the product possibly deriving from water.Significantly,further transformations of the product were conducted to showcase the utility of this electrosynthesis strategy.展开更多
基金National Natural Science Foundation of China(Nos.22301128 and 22301272)the Natural Science Foundation of Hunan Province(No.2022JJ40353)for financial support.
文摘An electrocatalytic 3,3-rearrangement/cyclization approach has been developed for the transformation of arylsubstituted propargylic aryl ethers to naphtho[1,2-b]furan-2-carbaldehyde and naphtho[2,1-b]furan-2-carbaldehyde derivatives.The reaction proceeded efficiently under mild conditions in the absence of metal-and chemicaloxidant,yielding the desired products with good substrate scope and functional group tolerance via a radical pathway.Furthermore,the control experiment revealed that the phenylselenyl-substituted secondary alcohol might be intermediate,and the ^(18)O labeling reaction indicated the oxygen source in the product possibly deriving from water.Significantly,further transformations of the product were conducted to showcase the utility of this electrosynthesis strategy.
