Annulation of Internal Alkyne toward Synthesis of Selective E-Benzofulvene and Mechanistic Study using Density Function Theory Calculation

Shubhendu Dhara*, Anuvab Das, Dhiraj Das, Rajesh Koner

DOI: 10.22607/IJACS.2021.903002

Volume 9, Issue 3 | Pages: 105-110

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Abstract

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.

Keywords
E-Benzofulvene Annulation Internal alkyne Wittig reaction o-bromostyrene Density function theory.
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Citation

Shubhendu Dhara*, Anuvab Das, Dhiraj Das, Rajesh Koner. Annulation of Internal Alkyne toward Synthesis of Selective E-Benzofulvene and Mechanistic Study using Density Function Theory Calculation. J Appl Pharm Sci. 2021; 9(3):105-110 .