Direct reductive aminations with catalytic molybdenum dioxide dichloride and phenylsilane

Clive A. Smith, Laura E. Cross, Kimberley Hughes, Rebecca E. Davis, Duncan B. Judd, Andrew T. Merritt

Research output: Contribution to journalArticle

23 Citations (Scopus)

Abstract

A powerful direct reductive amination (DRA) method is developed, using catalytic MoO2Cl2 and phenylsilane (PhSiH3) as the reducing agent. The alkylation of a range of amines (pK(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.
LanguageEnglish
Pages4906-4911
Number of pages5
JournalTetrahedron Letters
Volume50
Issue number34
DOIs
Publication statusPublished - 26 Aug 2009

Fingerprint

Amination
Electrons
Reducing Agents
Alkylation
Aldehydes
Functional groups
Amines
molybdenum dioxide
MoO2Cl2

Keywords

  • direct reductive amination (DRA)
  • molybdenum dioxide dichloride
  • phenylsilane
  • sodium triacetoxyborohydride
  • aryl PFP-sulfonate esters

Cite this

Smith, C. A., Cross, L. E., Hughes, K., Davis, R. E., Judd, D. B., & Merritt, A. T. (2009). Direct reductive aminations with catalytic molybdenum dioxide dichloride and phenylsilane. Tetrahedron Letters, 50(34), 4906-4911. https://doi.org/10.1016/j.tetlet.2009.06.071
Smith, Clive A. ; Cross, Laura E. ; Hughes, Kimberley ; Davis, Rebecca E. ; Judd, Duncan B. ; Merritt, Andrew T. / Direct reductive aminations with catalytic molybdenum dioxide dichloride and phenylsilane. In: Tetrahedron Letters. 2009 ; Vol. 50, No. 34. pp. 4906-4911.
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Smith, CA, Cross, LE, Hughes, K, Davis, RE, Judd, DB & Merritt, AT 2009, 'Direct reductive aminations with catalytic molybdenum dioxide dichloride and phenylsilane' Tetrahedron Letters, vol. 50, no. 34, pp. 4906-4911. https://doi.org/10.1016/j.tetlet.2009.06.071

Direct reductive aminations with catalytic molybdenum dioxide dichloride and phenylsilane. / Smith, Clive A.; Cross, Laura E.; Hughes, Kimberley; Davis, Rebecca E.; Judd, Duncan B.; Merritt, Andrew T.

In: Tetrahedron Letters, Vol. 50, No. 34, 26.08.2009, p. 4906-4911.

Research output: Contribution to journalArticle

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AU - Cross, Laura E.

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AU - Merritt, Andrew T.

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KW - molybdenum dioxide dichloride

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