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Indian Journal of Advances in Chemical Science, Volume: 9,
Issue :3, August 2021 |
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ISSN No.: 2320-0898 (Print);
2320-0928 (Electronic)
DOI: 10.22607/IJACS.2021.903002 |
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Research Article
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Annulation of Internal Alkyne toward Synthesis of Selective E-Benzofulvene
and Mechanistic Study using Density Function Theory Calculation |
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Shubhendu Dhara*, Anuvab Das, Dhiraj
Das, Rajesh Koner |
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ABSTRACT |
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An efficient approach has been devised
for the synthesis of highly functionalized E-benzofulvenes. While
annulating an internal alkyne with 4-(2-bromophenyl)but-3-en-2-one
yielded up to 87% of E-benzofulvene derivatives. Double
functionalization of Csp2-H and ortho-C-Br bonds in an α,β-unsaturated
arylketone in the presence of cheap catalyst PdCl2 with alkyne
triple bond afforded almost quantitative formation of highly
substituted benzofulvene in N,N-dimethylformamide solvent and under
reasonable reaction conditions. Detail mechanism of annulations of
alkynes to give selective E-benzofulvenes has been studied by
density function theory analysis using the Gaussian 09 program. |
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Key words: E-Benzofulvene, Annulation, Internal
alkyne, Wittig reaction, o-bromostyrene, Density function theory.
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[Download Full Article
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