Savio Cardoza, Parthasarathi Das, V. Tandon
Sep 16, 2019
Citations
0
Influential Citations
13
Citations
Journal
The Journal of organic chemistry
Abstract
Pd-catalyzed synthesis of multi-aryl 7-azaindoles using sequential arylation of 5-bromo-6-chloro-3-iodo-1-methyl-1H-pyrrolo[2,3-b] pyridine is established. Four diverse aryl groups are installed in chemo-selective fashion providing a general method to synthesize sterically encumbered compounds and extended 7-azaindoles in 48 - 95% yield. Three selective sequential arylations at C-3, C-5 and C-6 via Suzuki-Miyaura cross-coupling followed by direct C-2 arylation using Pd catalyst and AgOTf as an additive are highlights of the present work. Interestingly the tetra-aryl 7-azaindoles showed aggregate induced emission (AIE) making it potentially useful as fluorophores in OLEDs, sensors and bio-imaging tools.