Divergent Synthesis of Sulfonyl Quinolines, Formyl Indoles, and Quinolones from Ethynyl Benzoxazinanones via AuI Catalysis, AuI -Arl Co-Catalysis, and Silver Catalysis

The oxidative addition of Au-I with aromatic iodide (Ar-I) may generate reactive yet functional group tolerant Au-III catalysts (Ar-Au-III-I) in situ. Ar-Au-III-I may show different reactivity compared to Au-I catalysts and other transition metal catalysts. Our proof of concept application is the divergent synthesis of sulfonyl quinolines, formyl indoles, and quinolones from ethynyl benzoxazinanones via Au-I catalysis, Au-I-ArI co-catalysis, and silver catalysis. The chemo- and regioselectivity are good, and all the reactions can be conducted in the open air.

Automated summary

The oxidative addition of Au-I with aromatic iodide can generate reactive and functional group tolerant Au-III catalysts. These catalysts show different reactivity compared to Au-I catalysts and other transition metal catalysts. We demonstrated the synthesis of sulfonyl quinolines, formyl indoles, and quinolones using this catalytic system, which exhibited good chemo- and regioselectivity and could be conducted in the open air.