Palladium-catalyzed indium-mediated reductive aromatic C-H allylation of N-benzylsulfonimides with allyl esters

An unprecedented reductive aromatic C-H allylation reaction of benzyl electrophiles with allyl electrophiles has been established. A range of N-benzylsulfonimides smoothly participated in the palladium-catalyzed indium-mediated reductive aromatic C-H allylation with various allyl acetates, delivering structurally diverse allyl(hetero)arenes in moderate to excellent yields with good to excellent site selectivity. The use of inexpensive allyl esters for the reductive aromatic C-H allylation of N-benzylsulfonimides avoids the preparation of allyl organometallic reagents in advance and complements traditional functionalization of aromatic rings.

Automated summary

An unprecedented reductive aromatic C-H allylation reaction of benzyl electrophiles with allyl electrophiles has been developed. Various N-benzylsulfonimides smoothly participated in the reaction with allyl acetates under palladium-catalyzed indium-mediated conditions, delivering structurally diverse allyl(hetero)arenes in moderate to excellent yields with good to excellent site selectivity. The use of inexpensive allyl esters avoids the preparation of allyl organometallic reagents in advance and complements traditional functionalization of aromatic rings.