Construction of 3-Sulfonyl Naphthalenes via Tandem Reaction of 1,4-Diyn-3-yl Esters with Sodium Sulfinates

Polysubstituted 3-sulfonyl naphthalenes were constructed in good to high yields by AlCl3-mediated tandem reaction of 1,4-diyn-3-yl esters and sodium sulfinates. This reaction proceeded under mild reaction conditions and tolerated a variety of functional groups. Moreover, the mechanistic studies indicated that the initial formation of allene under DBU from 1,4-diyn-3-yl ester and a sequence of nucleophilic addition of sodium sulfinate, the formation of allene, and intramolecular cyclization might be involved.

Automated summary

In this study, polysubstituted 3-sulfonyl naphthalenes were efficiently synthesized in good to high yields via an AlCl3-mediated tandem reaction of 1,4-diyn-3-yl esters and sodium sulfinates. The reaction proceeded smoothly under mild conditions and tolerated various functional groups. The mechanistic studies suggested the involvement of initial allene formation, nucleophilic addition of sodium sulfinate, allene formation, and intramolecular cyclization.