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Practical Direct α‐Arylation of Cyclopentanones by Palladium/Enamine Cooperative Catalysis

Direct arylation of cyclopentanones has been a long‐standing challenge because of competitive self‐aldol condensation and multiple arylations. Reported herein is a direct mono‐α‐C−H arylation of cyclopentanones with aryl bromides which is enabled by palladium/amine cooperative catalysis. This method... Full description

Journal Title: Angewandte Chemie International Edition 12 February 2016, Vol.55(7), pp.2559-2563
Main Author: Xu, Yan
Other Authors: Su, Tianshun , Huang, Zhongxing , Dong, Guangbin
Format: Electronic Article Electronic Article
Language: English
Subjects:
ID: ISSN: 1433-7851 ; E-ISSN: 1521-3773 ; DOI: 10.1002/anie.201510638
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recordid: wj10.1002/anie.201510638
title: Practical Direct α‐Arylation of Cyclopentanones by Palladium/Enamine Cooperative Catalysis
format: Article
creator:
  • Xu, Yan
  • Su, Tianshun
  • Huang, Zhongxing
  • Dong, Guangbin
subjects:
  • Arylation
  • Homogeneous Catalysis
  • Ketones
  • Palladium
  • Synthetic Methods
ispartof: Angewandte Chemie International Edition, 12 February 2016, Vol.55(7), pp.2559-2563
description: Direct arylation of cyclopentanones has been a long‐standing challenge because of competitive self‐aldol condensation and multiple arylations. Reported herein is a direct mono‐α‐C−H arylation of cyclopentanones with aryl bromides which is enabled by palladium/amine cooperative catalysis. This method is scalable and chemoselective with broad functional‐group tolerance. Application to controlled sequential arylation of cyclopentanones has been also demonstrated. : A direct α‐C−H arylation of normal cyclopentanones with aryl bromides, enabled by palladium/amine cooperative catalysis, features an exceptionally high selectivity for monoarylation, use of readily available starting materials, good scalability, and broad functional‐group tolerance.
language: eng
source:
identifier: ISSN: 1433-7851 ; E-ISSN: 1521-3773 ; DOI: 10.1002/anie.201510638
fulltext: fulltext
issn:
  • 1433-7851
  • 14337851
  • 1521-3773
  • 15213773
url: Link


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subjectArylation ; Homogeneous Catalysis ; Ketones ; Palladium ; Synthetic Methods
descriptionDirect arylation of cyclopentanones has been a long‐standing challenge because of competitive self‐aldol condensation and multiple arylations. Reported herein is a direct mono‐α‐C−H arylation of cyclopentanones with aryl bromides which is enabled by palladium/amine cooperative catalysis. This method is scalable and chemoselective with broad functional‐group tolerance. Application to controlled sequential arylation of cyclopentanones has been also demonstrated. : A direct α‐C−H arylation of normal cyclopentanones with aryl bromides, enabled by palladium/amine cooperative catalysis, features an exceptionally high selectivity for monoarylation, use of readily available starting materials, good scalability, and broad functional‐group tolerance.
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descriptionDirect arylation of cyclopentanones has been a long‐standing challenge because of competitive self‐aldol condensation and multiple arylations. Reported herein is a direct mono‐α‐C−H arylation of cyclopentanones with aryl bromides which is enabled by palladium/amine cooperative catalysis. This method is scalable and chemoselective with broad functional‐group tolerance. Application to controlled sequential arylation of cyclopentanones has been also demonstrated. : A direct α‐C−H arylation of normal cyclopentanones with aryl bromides, enabled by palladium/amine cooperative catalysis, features an exceptionally high selectivity for monoarylation, use of readily available starting materials, good scalability, and broad functional‐group tolerance.
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abstractDirect arylation of cyclopentanones has been a long‐standing challenge because of competitive self‐aldol condensation and multiple arylations. Reported herein is a direct mono‐α‐C−H arylation of cyclopentanones with aryl bromides which is enabled by palladium/amine cooperative catalysis. This method is scalable and chemoselective with broad functional‐group tolerance. Application to controlled sequential arylation of cyclopentanones has been also demonstrated. : A direct α‐C−H arylation of normal cyclopentanones with aryl bromides, enabled by palladium/amine cooperative catalysis, features an exceptionally high selectivity for monoarylation, use of readily available starting materials, good scalability, and broad functional‐group tolerance.
doi10.1002/anie.201510638
pages2559-2563
date2016-02-12