N-Arylation of Aryl Mesylates and Monoarylation of Primary Amines Using BrettPhos

Buchwald and coworkers recently reported the use of a catalyst system comprised of the highly efficient ligand 2-(Dicyclohexylphosphino)3,6-dimethoxy-2′,4′,6′-triisopropyl- 1,1′-biphenyl (718742) (BrettPhos) and a palladium precatalyst (also containing the BrettPhos moiety) for the N-arylation of aryl mesylates with aryl amines (Scheme 4). Aryl mesylates constitute an important class of organic electrophiles due to their reasonable atom economy, cheap cost, and high stability. In addition, BrettPhos was found to be an effective ligand in the unprecedented monoarylation of primary amines with aryl chlorides at exceptionally low loadings (Scheme 5).


Scheme 4. Use of BrettPhos in the N-arylation of aryl mesylates with aryl amines

Scheme 4. Use of BrettPhos in the N-arylation of aryl mesylates with aryl amines (718742)

Scheme 5. Use of BrettPhos in the monoarylation of aryl chlorides and primary amines

Scheme 5. Use of BrettPhos in the monoarylation of aryl chlorides and primary amines (718742)

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Materials

     

References

  1. Fors, B. P.; Watson, D. A.; Biscoe, M. R.; Buchwald, S. L. J. Am. Chem. Soc. 2008, 130, 13552.

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