Migrative Thioamination of Aryne Intermediates Generated from o -Iodoaryl Triflates

Migrative thioamination of aryne intermediates takes place using various o-iodoaryl triflates and sulfilimines. The selective migra-tion realizes the facile synthesis of a broad range of highly functional-ized o-thioaminated diaryl sulfides. We succeeded in the ring expansion of cyclic sulfilimines enabling us to prepare eight-and nine-membered organosulfurs from dibenzothiophene-and thianthrene-type sulfilimi-nes, respectively.

Automated summary

Migrative thioamination of aryne intermediates using o-iodoaryl triflates and sulfilimines leads to the formation of highly functionalized o-thioaminated diaryl sulfides. The ring expansion of cyclic sulfilimines enables the synthesis of eight- and nine-membered organosulfur compounds from dibenzothiophene- and thianthrene-type sulfilimines, respectively.