Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 78, Issue 24, Pages 12703-12709Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo402304s
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Funding
- Kasetsart University Research and Development Institute (KURDI)
- Faculty of Science, Kasetsart University [ScRF-S5/2555]
- Thailand Research Fund
- National Center of Excellence for Petroleum, Petrochemical, and Advanced materials (NCE-PPAM)
- National Research University of Kasetsart University
- Center of Excellence for Innovation in Chemistry (PERCH-CIC), Commission on Higher Education, Ministry of Education
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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 sigma(p) values. DFT calculations reveal the origin of this effect, displaying smaller activation energy barriers for those pathways leading to the major regioisomer.
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