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Palladium-catalyzed Suzuki-Miyaura cross-coupling of secondary α-(trifluoromethyl)benzyl tosylates

Brambilla, Marta and Tredwell, Matthew 2017. Palladium-catalyzed Suzuki-Miyaura cross-coupling of secondary α-(trifluoromethyl)benzyl tosylates. Angewandte Chemie. International Edition 56 (39) , pp. 11981-11985. 10.1002/anie.201706631

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Abstract

A palladium‐catalyzed C(sp3)−C(sp2) Suzuki–Miyaura cross‐coupling of aryl boronic acids and α‐(trifluoromethyl)benzyl tosylates is reported. A readily available, air‐stable palladium catalyst was employed 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.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Medicine
Publisher: Wiley
ISSN: 1433-7851
Last Modified: 04 Sep 2019 13:05
URI: http://orca.cf.ac.uk/id/eprint/122201

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