Novel Brønsted Acid Catalyzed C-C Bond Activation and α-Alkylation of Ketones-Reference-Cited by-同舟云学术

Novel Brønsted Acid Catalyzed C-C Bond Activation and α-Alkylation of Ketones

Published:2024-09-09 Issue:17 Volume:29 Page:4266
ISSN:1420-3049
Container-title:Molecules
language:en
Short-container-title:Molecules

Author:

Li Wenjuan¹,Cheng Huihang¹,Han Huabo¹,Li Lu²,Liu Xinming²,Chu Xianxu¹,Li Xiaopei²

Affiliation:

1. Henan Key Laboratory of Biomolecular Recognition and Sensing, College of Chemistry and Chemical Engineering, Shangqiu Normal University, Shangqiu 476000, China

2. Henan Engineering Research Center of Green Synthesis for Pharmaceuticals, School of Chemistry and Chemical Engineering, Shangqiu Normal University, Shangqiu 476000, China

Abstract

A novel approach for the α-alkylation of ketones was developed using Brønsted acid-catalyzed C-C bond cleavage. Both aromatic and aliphatic ketones reacted smoothly with 2-substituted 1,3-diphenylpropane-1,3-diones to afford α-alkylation products with high yields and with excellent regioselectivity, in which the 1,3-dicarbonyl group acted as a leaving group in the presence of the catalyst TfOH. Mechanism experiments showed that the β-C-C bond cleavage of diketone and the shift of the equilibrium towards the enol formation from ketone are driving forces that induce the desired products.

Funder

Key Research and Development and Promotion Projects in Henan Province

Key Scientific Research Projects of Colleges and Universities in Henan Province

Publisher

MDPI AG

Link

https://www.mdpi.com/1420-3049/29/17/4266/pdf

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