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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Bibliographic Details
Published in:New journal of chemistry 2022-04, Vol.46 (17), p.7850-7854
Main Authors: Singh, Shikha, Trivedi, Laxmikant, Vasudev, Prema G., Passarella, Daniele, Negi, Arvind S.
Format: Article
Language:English
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