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

Brambilla, Marta; Tredwell, Matthew

doi:10.1002/anie.201706631

Item

ITEM ACTIONSEXPORT

Add to Basket

Please note that a newer version of this item is available:
https://pure.mpg.de/pubman/item/item_2468275_5

DetailsSummary

Released

Journal Article

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

MPS-Authors

/persons/resource/persons207420

Brambilla, Marta
Research Group Tredwell, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

/persons/resource/persons207366

Tredwell, Matthew
Research Group Tredwell, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

External Resource

No external resources are shared

Fulltext (restricted access)

There are currently no full texts shared for your IP range.

Fulltext (public)

There are no public fulltexts stored in PuRe

Supplementary Material (public)

There is no public supplementary material available

Citation

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

Cite as: https://hdl.handle.net/11858/00-001M-0000-002D-B0E6-8

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.