Visible Light‐Driven Difluoroalkoxylation of Imidazopyridines Using <i>N</i>‐Fluorobenzenesulfonimide as Fluorinating Agent

Abstract A visible‐light‐promoted site‐selective difluoroalkoxylation of imidazo[1,2‐a]pyridines has been achieved using N‐fluorobenzenesulfonimide (NFSI) as a fluorinating agent. This practical reaction has a wide range of substrate scope for both imidazo[1,2‐a]pyridines and alcohols to give 3,3‐difluoro‐2‐alkoxy‐2‐arylimidazo[1,2‐a]pyridines in 65–93% yields. The reaction proceeded at room temperature, showed high functional group tolerance, and was amenable to scale‐up. Based on mechanistic investigation, a radical pathway is proposed.

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Publication Details

Journal
Advanced Synthesis & Catalysis
Published
2024-08-29
DOI
https://doi.org/10.1002/adsc.202400755
Citations
5
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
1.25
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article

Visible Light‐Driven Difluoroalkoxylation of Imidazopyridines Using N‐Fluorobenzenesulfonimide as Fluorinating Agent

Bhawani, Krishnan Rangan, Anil Kumar, Vikki N. Shinde et al.
5 citations
Advanced Synthesis & Catalysis
Catalytic C–H Functionalization Methods
1.25
article

Visible Light‐Driven Difluoroalkoxylation of Imidazopyridines Using N‐Fluorobenzenesulfonimide as Fluorinating Agent

Bhawani, Krishnan Rangan, Anil Kumar, Vikki N. Shinde, Amol B. Gadekar, Sonam Sonam
article en
5 citations

Abstract

Abstract A visible‐light‐promoted site‐selective difluoroalkoxylation of imidazo[1,2‐a]pyridines has been achieved using N‐fluorobenzenesulfonimide (NFSI) as a fluorinating agent. This practical reaction has a wide range of substrate scope for both imidazo[1,2‐a]pyridines and alcohols to give 3,3‐difluoro‐2‐alkoxy‐2‐arylimidazo[1,2‐a]pyridines in 65–93% yields. The reaction proceeded at room temperature, showed high functional group tolerance, and was amenable to scale‐up. Based on mechanistic investigation, a radical pathway is proposed.

Advanced Synthesis & CatalysisVol. 366(22)
Birla Institute of Technology and Science - Hyderabad Campus (IN), Birla Institute of Technology and Science, Pilani (IN)
Clean water and sanitation
Openalex Percentile: Top 23%
Catalytic C–H Functionalization Methods
1.25
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