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.
An efficient merging of DBU/enolate and DBU/benzyl bromide organocycles for the synthesis of alpha benzylated 1-indanone derivatives / S. Singh, L. Trivedi, P.G. Vasudev, D. Passarella, A.S. Negi. - In: NEW JOURNAL OF CHEMISTRY. - ISSN 1144-0546. - 46:17(2022), pp. 7850-7854. [10.1039/d2nj00783e]
An efficient merging of DBU/enolate and DBU/benzyl bromide organocycles for the synthesis of alpha benzylated 1-indanone derivatives
D. Passarella;
2022
Abstract
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.File | Dimensione | Formato | |
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