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  Palladium Catalyzed Suzuki-Miyaura Cross-Coupling of Secondary α-(Trifluoromethyl)benzyl Tosylates

Brambilla, M., & Tredwell, M. (2017). Palladium Catalyzed Suzuki-Miyaura Cross-Coupling of Secondary α-(Trifluoromethyl)benzyl Tosylates. Angewandte Chemie International Edition, 56(39), 11981-11985. doi:10.1002/anie.201706631.

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Item Permalink: http://hdl.handle.net/11858/00-001M-0000-002D-B0E6-8 Version Permalink: http://hdl.handle.net/21.11116/0000-0004-59A7-C
Genre: Journal Article

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 Creators:
Brambilla, Marta1, Author              
Tredwell, Matthew1, Author              
Affiliations:
1Research Group Tredwell, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_2466692              

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Free keywords: cross-coupling; fluorine; homogeneous catalysis; palladium; transition-metal catalysis
 Abstract: A palladium catalyzed C(sp3)-C(sp2) Suzuki-Miyaura cross-coupling of aryl boronic acids and α-(trifluoromethyl)benzyl tosylates is reported. The reaction uses a readily available, air-stable palladium catalyst to access a wide range of functionalized 1,1-diaryl-2,2,2-trifluoroethanes. Enantioenriched α-(trifluoromethyl)benzyl tosylates were found to undergo cross-coupling to give the corresponding enantioenriched cross-coupled products with an overall inversion in configuration. The crucial role of the CF3 group in promoting this transformation is demonstrated by comparison with non-fluorinated derivatives.

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Language(s):
 Dates: 2017-06-292017-07-142017-07-142017-09-18
 Publication Status: Published in print
 Pages: 5
 Publishing info: -
 Table of Contents: -
 Rev. Method: Peer
 Identifiers: DOI: 10.1002/anie.201706631
 Degree: -

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Title: Angewandte Chemie International Edition
  Other : Angewandte Chemie, International Edition
  Other : Angew. Chem. Int. Ed.
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: 56 (39) Sequence Number: - Start / End Page: 11981 - 11985 Identifier: ISSN: 1433-7851
CoNE: https://pure.mpg.de/cone/journals/resource/1433-7851