DBU-catalyzed annulation strategy for modular assembly of 2,3-difunctionalized dihydrobenzofurans

An organocatalytic approach for the construction of 2,3-dihydrobenzofuran scaffold through a formal [4 + 1] annulation of 2-(2-nitrovinyl)phenols and α-bromoacetophenones in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) has been developed. This protocol could be easily performed in one mmol scale, giving a broad range of 2,3-dihydrobenzofuran derivatives in moderate to excellent yields and remarkable diastereoselectivity (>20 : 1 dr in general) with good functional group tolerance.

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Publication Details

Journal
Organic & Biomolecular Chemistry
Published
2025-01-01
DOI
https://doi.org/10.1039/d4ob01406e
Citations
2
Primary Topic
Synthetic Organic Chemistry Methods
Type
article
Field-Weighted Citation Impact
1.87

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article

DBU-catalyzed annulation strategy for modular assembly of 2,3-difunctionalized dihydrobenzofurans

Qiang Tang, Yiping Wang, Xinwei He, Beibei Ma et al.
2 citations
Organic & Biomolecular Chemistry
Synthetic Organic Chemistry Methods
1.87
article

DBU-catalyzed annulation strategy for modular assembly of 2,3-difunctionalized dihydrobenzofurans

Qiang Tang, Yiping Wang, Xinwei He, Beibei Ma, Yongjia Shang, Jie Wang, Lili Yuan
article en
2 citations

Abstract

An organocatalytic approach for the construction of 2,3-dihydrobenzofuran scaffold through a formal [4 + 1] annulation of 2-(2-nitrovinyl)phenols and α-bromoacetophenones in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) has been developed. This protocol could be easily performed in one mmol scale, giving a broad range of 2,3-dihydrobenzofuran derivatives in moderate to excellent yields and remarkable diastereoselectivity (>20 : 1 dr in general) with good functional group tolerance.

Organic & Biomolecular ChemistryVol. 23(8)
Wannan Medical College (CN), Hefei Normal University (CN), First Affiliated Hospital of Wannan Medical College (CN), Anhui Normal University (CN)
National Natural Science Foundation of China, Natural Science Foundation of Anhui Province
Clean water and sanitation
Openalex Percentile: Top 18%
Synthetic Organic Chemistry Methods
1.87
DOISourceOpenAlex
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DBU-catalyzed annulation strategy for modular assembly of 2,3-difunctionalized dihydrobenzofurans — Qiang Tang, Yiping Wang, et al. · Organic & Biomolecular Chemistry (2025) | TGRS Research Map | TGRS