posted on 2021-04-26, 17:07authored byAlexander
J. Rago, Guangbin Dong
Herein, we report the synthesis of
C3,C4-disubstituted indoles
via the palladium/norbornene cooperative catalysis. Utilizing N-benzoyloxy allylamines as the coupling partner, a cascade
process involving ortho-amination and ipso-Heck cyclization takes place with ortho-substituted
aryl iodides to afford diverse indole products. The reaction exhibits
good functional group tolerance, in addition to tolerating a removable
protecting group on the indole nitrogen. Divergent reactivity has
been observed using the allylamine coupling partner containing more
substituted olefins. Construction of the core framework of mitomycin
has also been attempted with this strategy.