Palladium-Catalyzed\nDouble <i>ipso</i>-Defluoroetherification\nof Allylic <i>gem</i>-Difluorides with Phenols or Alcohols

Significant progress has been made in the synthesis of\ndiverse\nketals through a palladium-catalyzed reaction involving allylic <i>gem</i>-difluorides and various phenols or alcohols. This methodology\nfacilitates double <i>ipso</i>-defluoroetherification of\nallylic <i>gem</i>-difluorides, resulting in high product\nyields with excellent regioselectivity. The reactions were conducted\nunder mild conditions and exhibited outstanding tolerance to a wide\nrange of functional groups. Notably, this approach overcomes the traditional\nlimitation of palladium-catalyzed processes, where nucleophiles typically\ntarget the common C-1 position of allylic <i>gem</i>-difluorides,\nenabling selective functionalization at the rare C-3 position instead.

Publication Details

Journal
Figshare
Published
2024-10-31
DOI
https://doi.org/10.1021/acs.orglett.4c03873.s001
Primary Topic
Fluorine in Organic Chemistry
Type
article
Field-Weighted Citation Impact
0.00
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article

Palladium-Catalyzed\nDouble ipso-Defluoroetherification\nof Allylic gem-Difluorides with Phenols or Alcohols

Figshare
Fluorine in Organic Chemistry
article

Palladium-Catalyzed\nDouble ipso-Defluoroetherification\nof Allylic gem-Difluorides with Phenols or Alcohols

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Abstract

Significant progress has been made in the synthesis of\ndiverse\nketals through a palladium-catalyzed reaction involving allylic <i>gem</i>-difluorides and various phenols or alcohols. This methodology\nfacilitates double <i>ipso</i>-defluoroetherification of\nallylic <i>gem</i>-difluorides, resulting in high product\nyields with excellent regioselectivity. The reactions were conducted\nunder mild conditions and exhibited outstanding tolerance to a wide\nrange of functional groups. Notably, this approach overcomes the traditional\nlimitation of palladium-catalyzed processes, where nucleophiles typically\ntarget the common C-1 position of allylic <i>gem</i>-difluorides,\nenabling selective functionalization at the rare C-3 position instead.

Figshare
Openalex Percentile: Top 77%
Fluorine in Organic Chemistry
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