Facile Approachto Diverse Diarylmethane Scaffoldsvia DBU-Catalyzed 1,6-Addition Reaction: Discovery of an AntibacterialAgent

Herein, a DBU-catalyzed 1,6-Michael addition of para-quinone methides (p-QMs) under mild reaction conditions with high efficiency (turnover number up to 10<sup>3</sup>) and good to excellent yields is reported. The transformation proceeds smoothly with a range of nucleophiles, providing diverse diarylmethane scaffolds with good efficiency. Mechanistic studies revealed that DBU is an excellent proton acceptor and donor and that DBU can promote the addition of methanol to <i>p</i>-QMs. A preliminary investigation was also conducted of the antibacterial properties of the products.

Publication Details

Journal
Figshare
Published
2025-01-15
DOI
https://doi.org/10.1021/acsomega.4c09847.s001
Primary Topic
Synthesis of Indole Derivatives
Type
article
Field-Weighted Citation Impact
0.00
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article

Facile Approachto Diverse Diarylmethane Scaffoldsvia DBU-Catalyzed 1,6-Addition Reaction: Discovery of an AntibacterialAgent

Figshare
Synthesis of Indole Derivatives
article

Facile Approachto Diverse Diarylmethane Scaffoldsvia DBU-Catalyzed 1,6-Addition Reaction: Discovery of an AntibacterialAgent

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Abstract

Herein, a DBU-catalyzed 1,6-Michael addition of para-quinone methides (p-QMs) under mild reaction conditions with high efficiency (turnover number up to 10<sup>3</sup>) and good to excellent yields is reported. The transformation proceeds smoothly with a range of nucleophiles, providing diverse diarylmethane scaffolds with good efficiency. Mechanistic studies revealed that DBU is an excellent proton acceptor and donor and that DBU can promote the addition of methanol to <i>p</i>-QMs. A preliminary investigation was also conducted of the antibacterial properties of the products.

Figshare
Openalex Percentile: Top 68%
Synthesis of Indole Derivatives
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Facile Approachto Diverse Diarylmethane Scaffoldsvia DBU-Catalyzed 1,6-Addition Reaction: Discovery of an AntibacterialAgent · Figshare (2025) | TGRS Research Map | TGRS