Palladium-Catalyzed Double <i>ipso</i>-Defluoroetherification of Allylic <i>gem</i>-Difluorides with Phenols or Alcohols

Significant progress has been made in the synthesis of diverse ketals through a palladium-catalyzed reaction involving allylic <i>gem</i>-difluorides and various phenols or alcohols. This methodology facilitates double <i>ipso</i>-defluoroetherification of allylic <i>gem</i>-difluorides, resulting in high product yields with excellent regioselectivity. The reactions were conducted under mild conditions and exhibited outstanding tolerance to a wide range of functional groups. Notably, this approach overcomes the traditional limitation of palladium-catalyzed processes, where nucleophiles typically target the common C-1 position of allylic <i>gem</i>-difluorides, enabling selective functionalization at the rare C-3 position instead.

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Publication Details

Journal
Organic Letters
Published
2024-10-31
DOI
https://doi.org/10.1021/acs.orglett.4c03873
Citations
7
Primary Topic
Fluorine in Organic Chemistry
Type
article
Field-Weighted Citation Impact
1.46

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article

Palladium-Catalyzed Double ipso-Defluoroetherification of Allylic gem-Difluorides with Phenols or Alcohols

Luning Tang, S. Chen, Ming Chen
7 citations
Organic Letters
Fluorine in Organic Chemistry
1.46
article

Palladium-Catalyzed Double ipso-Defluoroetherification of Allylic gem-Difluorides with Phenols or Alcohols

Luning Tang, S. Chen, Ming Chen
article en
7 citations

Abstract

Significant progress has been made in the synthesis of diverse ketals through a palladium-catalyzed reaction involving allylic <i>gem</i>-difluorides and various phenols or alcohols. This methodology facilitates double <i>ipso</i>-defluoroetherification of allylic <i>gem</i>-difluorides, resulting in high product yields with excellent regioselectivity. The reactions were conducted under mild conditions and exhibited outstanding tolerance to a wide range of functional groups. Notably, this approach overcomes the traditional limitation of palladium-catalyzed processes, where nucleophiles typically target the common C-1 position of allylic <i>gem</i>-difluorides, enabling selective functionalization at the rare C-3 position instead.

Organic LettersVol. 26(45)
Changzhou University (CN)
National Natural Science Foundation of China, Changzhou University
Clean water and sanitation
Openalex Percentile: Top 20%
Fluorine in Organic Chemistry
1.46
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Palladium-Catalyzed Double <i>ipso</i>-Defluoroetherification of Allylic <i>gem</i>-Difluorides with Phenols or Alcohols — Luning Tang, S. Chen, et al. · Organic Letters (2024) | TGRS Research Map | TGRS