Palladium and Raney Nickel Catalyzed Methanolic Cleavage of Stable Borane-Amine Complexes

Organic Letters

Volumn 3, Issue 3, 2001, Pages 465-467

  Couturier, Michel ^a   Tucker, John L ^a   Andresen, Brian M ^a   Dubé, Pascal ^a,b   Negri, Joanna T ^a  

^a PFIZER INC   (United States)

^b UNIVERSITÉ DE SHERBROOKE   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001262709     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006969+     Document Type: Article

References (44)

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42. Prerared from corresponding amide reduction and/or amine complexation with borane-THF.
43. General Procedure. To a magnetically stirred solution of borane-amine complex (5.0 mmol) and, optionally, 1-hexene (25.0 mmol) in methanol (10 mL) was added Raney nickel (5.0 mol%) or 10% palladium on charcoal (1.0 mol %). Upon completion, the reaction mixture was filtered over a small pad of Celite and the latter was rinsed with methanol (5.0 mL). The concentrated residue was purified by "flash" silica chromatography to yield the desired amine.
44. Olefins and alkynes containing substrates might be prone to hydrogenation under these reaction conditions.