TY - JOUR
T1 - Pd-Catalyzed Indolization/peri-C–H Annulation/N-Dealkylation Cascade to Cyclopenta-Fused Acenaphtho[1,2-b]indole Scaffold
AU - Jin, Tienan
AU - Suzuki, Shin
AU - Ho, Hon Eong
AU - Matsuyama, Hidenori
AU - Kawata, Masaki
AU - Terada, Masahiro
N1 - Funding Information:
This research was supported by a Grant-in-Aid for Scientific Research on Innovative Areas “Hybrid Catalysis for Enabling Molecular Synthesis on Demand” (JP17H06447) from MEXT (Japan) and a Grant-in-Aid for Scientific Research (S) (JP16H06354) from the JSPS.
Publisher Copyright:
© 2021 American Chemical Society
PY - 2021/12/17
Y1 - 2021/12/17
N2 - 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.
AB - 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.
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U2 - 10.1021/acs.orglett.1c03575
DO - 10.1021/acs.orglett.1c03575
M3 - Article
C2 - 34851130
AN - SCOPUS:85120855837
SN - 1523-7060
VL - 23
SP - 9431
EP - 9435
JO - Organic Letters
JF - Organic Letters
IS - 24
ER -