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Lanthanum Tricyanide-Catalyzed Acyl Silane-Ketone Benzoin Additions

James C. Tarr and Jeffrey S. Johnson*

*Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, Email:

J. C. Tarr, J. S. Johnson, Org. Lett., 2009, 11, 3870-3873.

DOI: 10.1021/ol901314w


Lanthanum tricyanide efficiently catalyzes a benzoin-type coupling between acyl silanes and ketones. Good yields are obtained over a broad substrate scope encompassing aryl, alkyl, and sterically hindered ketones.

see article for more examples

proposed mechanism

Catalytic Nucleophilic Glyoxylation of Aldehydes

K. M. Steward, J. S. Johnson, Org. Lett., 2010, 12, 2864-2867.

Kinetic Control in Direct α-Silyloxy Ketone Synthesis: A New Regiospecific Catalyzed Cross Silyl Benzoin Reaction

X. Linghu, J. S. Johnson, Angew. Chem. Int. Ed., 2003, 42, 2534-2536.

Key Words

Benzoins, Benzoin Condensation, Brook Rearrangement

ID: J54-Y2009-2620