Direct reductive aminations with catalytic molybdenum dioxide dichloride and phenylsilane

A powerful direct reductive amination (DRA) method is developed, using catalytic MoO 2Cl 2 and with PhSiH 3 as the reducing agent. A powerful direct reductive amination (DRA) method is developed, using catalytic MoO 2Cl 2 and phenylsilane (PhSiH 3) as the reducing agent. The alkylation of a range of...

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Bibliographic Details
Published inTetrahedron letters Vol. 50; no. 34; pp. 4906 - 4911
Main Authors Smith, Clive A., Cross, Laura E., Hughes, Kimberley, Davis, Rebecca E., Judd, Duncan B., Merritt, Andrew T.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 26.08.2009
Elsevier
Subjects
Aryl PFP-sulfonate esters
Chemistry
Chemistry, Organic
Direct reductive amination (DRA)
Molybdenum dioxide dichloride
Phenylsilane
Physical Sciences
Science & Technology
Sodium triacetoxyborohydride
Direct reductive amination (DRA)
Phenylsilane
Sodium triacetoxyborohydride
Aryl PFP-sulfonate esters
Molybdenum dioxide dichloride
SYSTEM
COMPLEX
IMINES
HYDROSILYLATION
CARBONYL-COMPOUNDS
TRANSFER HYDROGENATION
ALDEHYDES
KETONES
SULFONATE ESTERS
EFFICIENT REAGENT COMBINATION
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Summary:A powerful direct reductive amination (DRA) method is developed, using catalytic MoO 2Cl 2 and with PhSiH 3 as the reducing agent. A powerful direct reductive amination (DRA) method is developed, using catalytic MoO 2Cl 2 and phenylsilane (PhSiH 3) as the reducing agent. The alkylation of a range of amines (p K a 0–7.8) with both an electron-deficient and two electron-rich-aldehydes is achieved in good to excellent yields. The novel employment of this DRA in alcoholic solvents significantly improves the reaction scope and excellent functional group selectivity is exhibited.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2009.06.071