Palladium‐Based Dyotropic Rearrangement Enables A Triple Functionalization of Gem‐Disubstituted Alkenes: An Unusual Fluorolactonization Reaction

We report in this paper a Pd(II)‐catalyzed migratory gem‐fluorolactonization of ene‐carboxylic acids. Reaction of 4‐methylenealkanoic acid derivatives with Selectfluor in the presence of Pd(OAc)2 (1.0 mol %) at room temperature affords fluorolactones in good to excellent yields. 2‐(2‐Methylenecycloa...

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Published inAngewandte Chemie International Edition Vol. 63; no. 1; pp. e202316393 - n/a
Main Authors Feng, Qiang, Liu, Chen‐Xu, Wang, Qian, Zhu, Jieping
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 02.01.2024
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
1-Fluoroalkylcarboxylate
Acetic acid
Alkenes
Carbon
Carboxylic acids
Chemistry
Chemistry, Multidisciplinary
Dyotropic Rearrangement
Fluorination
Fluorolactonization
High Valent Palladium
Oxidation
Palladium
Physical Sciences
Room temperature
Science & Technology
Dyotropic Rearrangement
High Valent Palladium
SYMMETRY CONTROLLED REACTIONS
DIACETOXYLATION
C-H FLUORINATION
Fluorolactonization
LACTONIZATION
Fluorination
DERIVATIVES
1-Fluoroalkylcarboxylate
CARBOXYLIC-ACIDS
DIFLUORINATION
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Abstract We report in this paper a Pd(II)‐catalyzed migratory gem‐fluorolactonization of ene‐carboxylic acids. Reaction of 4‐methylenealkanoic acid derivatives with Selectfluor in the presence of Pd(OAc)2 (1.0 mol %) at room temperature affords fluorolactones in good to excellent yields. 2‐(2‐Methylenecycloalkanyl)acetic acids are transformed to bridged fluorolactones under identical conditions. One C−C, one C−O and one tertiary C−F bond were generated along the gem‐disubstituted carbon‐carbon double bond in this operationally simple transformation. Trapping experiments indicates that the reaction is initiated by a 5‐exo‐trig oxypalladation followed by Pd oxidation, regioselective ring‐enlarging 1,2‐alkyl/Pd(IV) dyotropic rearrangement and C−F bond forming reductive elimination cascade. Post‐transformations of these fluorolactones taking advantage of the electrophilicity of the 1‐fluoroalkylcarboxylate function are also documented. Pd‐catalyzed reaction of 4‐methylenealkanoic acid derivatives with Selectfluor provides fluorolactones via a sequence of 5‐exo‐trig oxypalladation, Pd oxidation, regioselective ring‐enlarging 1,2‐alkyl/Pd(IV) dyotropic rearrangement and C−F bond‐forming reductive elimination.
AbstractList We report in this paper a Pd(II)-catalyzed migratory gem-fluorolactonization of ene-carboxylic acids. Reaction of 4-methylenealkanoic acid derivatives with Selectfluor in the presence of Pd(OAc) (1.0 mol %) at room temperature affords fluorolactones in good to excellent yields. 2-(2-Methylenecycloalkanyl)acetic acids are transformed to bridged fluorolactones under identical conditions. One C-C, one C-O and one tertiary C-F bond were generated along the gem-disubstituted carbon-carbon double bond in this operationally simple transformation. Trapping experiments indicates that the reaction is initiated by a 5-exo-trig oxypalladation followed by Pd oxidation, regioselective ring-enlarging 1,2-alkyl/Pd(IV) dyotropic rearrangement and C-F bond forming reductive elimination cascade. Post-transformations of these fluorolactones taking advantage of the electrophilicity of the 1-fluoroalkylcarboxylate function are also documented.
We report in this paper a Pd(II)‐catalyzed migratory gem‐fluorolactonization of ene‐carboxylic acids. Reaction of 4‐methylenealkanoic acid derivatives with Selectfluor in the presence of Pd(OAc) 2 (1.0 mol %) at room temperature affords fluorolactones in good to excellent yields. 2‐(2‐Methylenecycloalkanyl)acetic acids are transformed to bridged fluorolactones under identical conditions. One C−C, one C−O and one tertiary C−F bond were generated along the gem‐disubstituted carbon‐carbon double bond in this operationally simple transformation. Trapping experiments indicates that the reaction is initiated by a 5‐exo‐trig oxypalladation followed by Pd oxidation, regioselective ring‐enlarging 1,2‐alkyl/Pd(IV) dyotropic rearrangement and C−F bond forming reductive elimination cascade. Post‐transformations of these fluorolactones taking advantage of the electrophilicity of the 1‐fluoroalkylcarboxylate function are also documented.
We report in this paper a Pd(II)‐catalyzed migratory gem‐fluorolactonization of ene‐carboxylic acids. Reaction of 4‐methylenealkanoic acid derivatives with Selectfluor in the presence of Pd(OAc)2 (1.0 mol %) at room temperature affords fluorolactones in good to excellent yields. 2‐(2‐Methylenecycloalkanyl)acetic acids are transformed to bridged fluorolactones under identical conditions. One C−C, one C−O and one tertiary C−F bond were generated along the gem‐disubstituted carbon‐carbon double bond in this operationally simple transformation. Trapping experiments indicates that the reaction is initiated by a 5‐exo‐trig oxypalladation followed by Pd oxidation, regioselective ring‐enlarging 1,2‐alkyl/Pd(IV) dyotropic rearrangement and C−F bond forming reductive elimination cascade. Post‐transformations of these fluorolactones taking advantage of the electrophilicity of the 1‐fluoroalkylcarboxylate function are also documented.
We report in this paper a Pd(II)-catalyzed migratory gem-fluorolactonization of ene-carboxylic acids. Reaction of 4-methylenealkanoic acid derivatives with Selectfluor in the presence of Pd(OAc)2 (1.0 mol %) at room temperature affords fluorolactones in good to excellent yields. 2-(2-Methylenecycloalkanyl)acetic acids are transformed to bridged fluorolactones under identical conditions. One C-C, one C-O and one tertiary C-F bond were generated along the gem-disubstituted carbon-carbon double bond in this operationally simple transformation. Trapping experiments indicates that the reaction is initiated by a 5-exo-trig oxypalladation followed by Pd oxidation, regioselective ring-enlarging 1,2-alkyl/Pd(IV) dyotropic rearrangement and C-F bond forming reductive elimination cascade. Post-transformations of these fluorolactones taking advantage of the electrophilicity of the 1-fluoroalkylcarboxylate function are also documented.We report in this paper a Pd(II)-catalyzed migratory gem-fluorolactonization of ene-carboxylic acids. Reaction of 4-methylenealkanoic acid derivatives with Selectfluor in the presence of Pd(OAc)2 (1.0 mol %) at room temperature affords fluorolactones in good to excellent yields. 2-(2-Methylenecycloalkanyl)acetic acids are transformed to bridged fluorolactones under identical conditions. One C-C, one C-O and one tertiary C-F bond were generated along the gem-disubstituted carbon-carbon double bond in this operationally simple transformation. Trapping experiments indicates that the reaction is initiated by a 5-exo-trig oxypalladation followed by Pd oxidation, regioselective ring-enlarging 1,2-alkyl/Pd(IV) dyotropic rearrangement and C-F bond forming reductive elimination cascade. Post-transformations of these fluorolactones taking advantage of the electrophilicity of the 1-fluoroalkylcarboxylate function are also documented.
We report in this paper a Pd(II)‐catalyzed migratory gem‐fluorolactonization of ene‐carboxylic acids. Reaction of 4‐methylenealkanoic acid derivatives with Selectfluor in the presence of Pd(OAc)2 (1.0 mol %) at room temperature affords fluorolactones in good to excellent yields. 2‐(2‐Methylenecycloalkanyl)acetic acids are transformed to bridged fluorolactones under identical conditions. One C−C, one C−O and one tertiary C−F bond were generated along the gem‐disubstituted carbon‐carbon double bond in this operationally simple transformation. Trapping experiments indicates that the reaction is initiated by a 5‐exo‐trig oxypalladation followed by Pd oxidation, regioselective ring‐enlarging 1,2‐alkyl/Pd(IV) dyotropic rearrangement and C−F bond forming reductive elimination cascade. Post‐transformations of these fluorolactones taking advantage of the electrophilicity of the 1‐fluoroalkylcarboxylate function are also documented. Pd‐catalyzed reaction of 4‐methylenealkanoic acid derivatives with Selectfluor provides fluorolactones via a sequence of 5‐exo‐trig oxypalladation, Pd oxidation, regioselective ring‐enlarging 1,2‐alkyl/Pd(IV) dyotropic rearrangement and C−F bond‐forming reductive elimination.
We report in this paper a Pd(II)-catalyzed migratory gem-fluorolactonization of ene-carboxylic acids. Reaction of 4-methylenealkanoic acid derivatives with Selectfluor in the presence of Pd(OAc)(2) (1.0 mol %) at room temperature affords fluorolactones in good to excellent yields. 2-(2-Methylenecycloalkanyl)acetic acids are transformed to bridged fluorolactones under identical conditions. One C-C, one C-O and one tertiary C-F bond were generated along the gem-disubstituted carbon-carbon double bond in this operationally simple transformation. Trapping experiments indicates that the reaction is initiated by a 5-exo-trig oxypalladation followed by Pd oxidation, regioselective ring-enlarging 1,2-alkyl/Pd(IV) dyotropic rearrangement and C-F bond forming reductive elimination cascade. Post-transformations of these fluorolactones taking advantage of the electrophilicity of the 1-fluoroalkylcarboxylate function are also documented.
Author Feng, Qiang
Wang, Qian
Liu, Chen‐Xu
Zhu, Jieping
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  surname: Liu
  fullname: Liu, Chen‐Xu
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  surname: Zhu
  fullname: Zhu, Jieping
  email: jieping.zhu@epfl.ch
  organization: Ecole Polytechnique Fédérale de Lausanne
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Issue 1
Keywords Dyotropic Rearrangement
High Valent Palladium
SYMMETRY CONTROLLED REACTIONS
DIACETOXYLATION
C-H FLUORINATION
Fluorolactonization
LACTONIZATION
Fluorination
DERIVATIVES
1-Fluoroalkylcarboxylate
CARBOXYLIC-ACIDS
DIFLUORINATION
Language English
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SSID ssj0028806
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Snippet We report in this paper a Pd(II)‐catalyzed migratory gem‐fluorolactonization of ene‐carboxylic acids. Reaction of 4‐methylenealkanoic acid derivatives with...
We report in this paper a Pd(II)-catalyzed migratory gem-fluorolactonization of ene-carboxylic acids. Reaction of 4-methylenealkanoic acid derivatives with...
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SubjectTerms 1-Fluoroalkylcarboxylate
Acetic acid
Alkenes
Carbon
Carboxylic acids
Chemistry
Chemistry, Multidisciplinary
Dyotropic Rearrangement
Fluorination
Fluorolactonization
High Valent Palladium
Oxidation
Palladium
Physical Sciences
Room temperature
Science & Technology
Title Palladium‐Based Dyotropic Rearrangement Enables A Triple Functionalization of Gem‐Disubstituted Alkenes: An Unusual Fluorolactonization Reaction
URI https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fanie.202316393
http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=001110708400001
https://www.ncbi.nlm.nih.gov/pubmed/37986261
https://www.proquest.com/docview/2906655615
https://www.proquest.com/docview/2892267943
Volume 63
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