BF<sub>3</sub>·OEt<sub>2</sub> Promoted 1,6‐Conjugate Addition of <i>para</i>‐Quinone Methides: A Regioselective Approach to Diarylmethyl‐Substituted Carbo‐ and Heterocycles

In this work, we report a base-free and transition metal-free 1,6-conjugate addition strategy for synthesizing unsymmetrical diaryl-substituted methanes possessing carbo- and heterocycles such as 1,3-indandione, aminouracils, and barbituric acid derivatives from para-quinone methides (p-QMs) using BF<sub>3</sub>·OEt<sub>2</sub> as promoter. The high functional group tolerance, good to excellent yields, and mild reaction conditions of this protocol underscore its significant potential for the synthesis of a broad spectrum of titled products. Furthermore, gram-scale synthesis and versatile subsequent conversions highlight the synthetic utility of these scaffolds.

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Publication Details

Journal
Chemistry - An Asian Journal
Published
2025-06-13
DOI
https://doi.org/10.1002/asia.202500595
Citations
4
Primary Topic
Synthesis of Indole Derivatives
Type
article
Field-Weighted Citation Impact
3.74

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article

BF3·OEt2 Promoted 1,6‐Conjugate Addition of para‐Quinone Methides: A Regioselective Approach to Diarylmethyl‐Substituted Carbo‐ and Heterocycles

Rajnish Budhwan, Rama Krishna Peddinti, Megha Rawat, Anoop Yadav
4 citations
Chemistry - An Asian Journal
Synthesis of Indole Derivatives
3.74
article

BF3·OEt2 Promoted 1,6‐Conjugate Addition of para‐Quinone Methides: A Regioselective Approach to Diarylmethyl‐Substituted Carbo‐ and Heterocycles

Rajnish Budhwan, Rama Krishna Peddinti, Megha Rawat, Anoop Yadav
article en
4 citations

Abstract

In this work, we report a base-free and transition metal-free 1,6-conjugate addition strategy for synthesizing unsymmetrical diaryl-substituted methanes possessing carbo- and heterocycles such as 1,3-indandione, aminouracils, and barbituric acid derivatives from para-quinone methides (p-QMs) using BF<sub>3</sub>·OEt<sub>2</sub> as promoter. The high functional group tolerance, good to excellent yields, and mild reaction conditions of this protocol underscore its significant potential for the synthesis of a broad spectrum of titled products. Furthermore, gram-scale synthesis and versatile subsequent conversions highlight the synthetic utility of these scaffolds.

Chemistry - An Asian JournalVol. 20(17)
Indian Institute of Technology Roorkee (IN)
Indian Institute of Technology Roorkee, Science and Engineering Research Board
Openalex Percentile: Top 7%
Synthesis of Indole Derivatives
3.74
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BF<sub>3</sub>·OEt<sub>2</sub> Promoted 1,6‐Conjugate Addition of <i>para</i>‐Quinone Methides: A Regioselective Approach to Diarylmethyl‐Substituted Carbo‐ and Heterocycles — Rajnish Budhwan, Rama Krishna Peddinti, et al. · Chemistry - An Asian Journal (2025) | TGRS Research Map | TGRS