Copper-Catalyzed Sulfonylation/Cyclization of Pent-4-ynamides toward Sulfonyl-Functionalized Pyrrol-2-ones

A domino sulfonylation/intramolecular C-N coupling/ dehydrogenation reaction was realized between pent-4-ynamides and sulfonyl chlorides by catalysis of Cu(acac)2 and 2,2 '-bis-(diphenylphosphanyl)-1,1 '-binaphthalene. The reaction provides a convenient approach to sulfonyl-functionalized pyrrol-2-ones. This method can also be applied to the synthesis of 3-alkylidene isoindolinones from 2-ethynyl-benzamides.

Automated summary

A domino sulfonylation/intramolecular C-N coupling/dehydrogenation reaction was achieved between pent-4-ynamides and sulfonyl chlorides, catalyzed by Cu(acac)2 and 2,2'-bis-(diphenylphosphanyl)-1,1'-binaphthalene. The reaction offers a convenient approach to sulfonyl-functionalized pyrrol-2-ones. This method can also be used for the synthesis of 3-alkylidene isoindolinones from 2-ethynyl-benzamides.