Publication: Regioselectivity of Larock heteroannulation: A contribution from electronic properties of diarylacetylenes
Issued Date
2013-12-20
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ISSN
15206904
00223263
00223263
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2-s2.0-84890911121
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Mahidol University
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SCOPUS
Bibliographic Citation
Journal of Organic Chemistry. Vol.78, No.24 (2013), 12703-12709
Suggested Citation
Nared Phetrak, Thanya Rukkijakan, Jakkapan Sirijaraensre, Samran Prabpai, Palangpon Kongsaeree, Chayada Klinchan, Pitak Chuawong Regioselectivity of Larock heteroannulation: A contribution from electronic properties of diarylacetylenes. Journal of Organic Chemistry. Vol.78, No.24 (2013), 12703-12709. doi:10.1021/jo402304s Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/31501
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Title
Regioselectivity of Larock heteroannulation: A contribution from electronic properties of diarylacetylenes
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Abstract
A 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.