An efficient merging of DBU/enolate and DBU/benzyl bromide organocycles for the synthesis of alpha benzylated 1-indanone derivatives

The merging of dual organocycles of the bicyclic amidine base 1,8-diazabicyclo[5.4.0]undec-7-en (DBU) was demonstrated for the synthesis of alpha-benzylated 1-indanones. A highly reactive enolate intermediate was formed in the presence of DBU, which reacted with DBU/benzyl bromide salt to afford the...

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Published inNew journal of chemistry Vol. 46; no. 17; pp. 7850 - 7854
Main Authors Singh, Shikha, Trivedi, Laxmikant, Vasudev, Prema G., Passarella, Daniele, Negi, Arvind S.
Format Journal Article
LanguageEnglish
Published Cambridge Royal Society of Chemistry 04.04.2022
Subjects
Benzyl bromide
Low temperature
Reagents
Substrates
Synthesis
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Summary:The merging of dual organocycles of the bicyclic amidine base 1,8-diazabicyclo[5.4.0]undec-7-en (DBU) was demonstrated for the synthesis of alpha-benzylated 1-indanones. A highly reactive enolate intermediate was formed in the presence of DBU, which reacted with DBU/benzyl bromide salt to afford the product at 50 °C temperature. This simple and straightforward transformation using safer DBU reagent with easily available substrates and excellent yield provides a better alternative to the previously reported methods that required pyrophoric, costly reagents and high or very low-temperature reaction conditions. CIMAP Communication number: CIMAP/PUB/2022/3.
ISSN:1144-0546
1369-9261
DOI:10.1039/D2NJ00783E