A new nucleophilic 1,3-rearrangement is observed when treating 2-methoxyquinolino-3-lithium with an α-C substituted deoxybenzoin,and this rearrangement yielded an unusual 3,4-disubstituted 3,4-dihydroquinoline.Severa...A new nucleophilic 1,3-rearrangement is observed when treating 2-methoxyquinolino-3-lithium with an α-C substituted deoxybenzoin,and this rearrangement yielded an unusual 3,4-disubstituted 3,4-dihydroquinoline.Several similar reactions were designed and executed to investigate this novel 1,3-rearrangement,and a mechanism involving a nucleophilic addition and a following 1,3-rearrangement with an unusual dearomatization on the quinoline ring is proposed.展开更多
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‘‘The National High-Tech Research and Development Program (‘‘863’’Program) of China’’No. 2012AA020302) for financial support
文摘A new nucleophilic 1,3-rearrangement is observed when treating 2-methoxyquinolino-3-lithium with an α-C substituted deoxybenzoin,and this rearrangement yielded an unusual 3,4-disubstituted 3,4-dihydroquinoline.Several similar reactions were designed and executed to investigate this novel 1,3-rearrangement,and a mechanism involving a nucleophilic addition and a following 1,3-rearrangement with an unusual dearomatization on the quinoline ring is proposed.
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.
