posted on 2021-12-01, 15:04authored byTienan Jin, Shin Suzuki, Hon Eong Ho, Hidenori Matsuyama, Masaki Kawata, Masahiro Terada
A novel Pd-catalyzed cascade reaction
of N,N-dialkyl-substituted o-alkynylanilines
involving an indolization/peri-C–H annulation/N-dealkylation sequence has been developed to construct
a cyclopenta-fused acenaphtho[1,2-b]indole (ANI)
scaffold. A variety of aromatic hydrocarbons having a peri-C–H bond at the alkynyl terminus, such as naphthalene, phenanthrene,
pyrene, and fluoranthene, were employed, affording the corresponding
π-extended ANI derivatives. The ANI molecules showed relatively
narrow energy gaps by increasing HOMOs and lowering LUMOs, implying
their potential applications as π-segments in low-band-gap materials.