Nared PhetrakThanya RukkijakanJakkapan SirijaraensreSamran PrabpaiPalangpon KongsaereeChayada KlinchanPitak ChuawongFaculty of EngineeringKasetsart UniversityMahidol University2018-10-192018-10-192013-12-20Journal of Organic Chemistry. Vol.78, No.24 (2013), 12703-1270915206904002232632-s2.0-84890911121https://repository.li.mahidol.ac.th/handle/20.500.14594/31501A series of 2,3-diarylindoles were synthesized from 2-iodoaniline and unsymmetrical diarylacetylenes using the Larock heteroannulation. Diarylacetylenes bearing electron-withdrawing substituents lead to 2,3-diarylindoles with substituted phenyl moieties at the 2-position as major products, while those with electron-donating groups preferably yield indole products with substituted phenyl moieties at the 3-position. The regioisomeric product ratios exhibit a clear correlation with Hammett σp values. DFT calculations reveal the origin of this effect, displaying smaller activation energy barriers for those pathways leading to the major regioisomer. © 2013 American Chemical Society.Mahidol UniversityChemistryArticleSCOPUS10.1021/jo402304s