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

doi:10.1016/j.tetlet.2009.06.071

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

Faculty Of Science

Research output: Contribution to journal › Article › peer-review

27 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.

Original language	English
Pages (from-to)	4906-4911
Number of pages	5
Journal	Tetrahedron Letters
Volume	50
Issue number	34
DOIs	https://doi.org/10.1016/j.tetlet.2009.06.071
Publication status	Published - 26 Aug 2009

Keywords

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

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10.1016/j.tetlet.2009.06.071

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title = "Direct reductive aminations with catalytic molybdenum dioxide dichloride and phenylsilane",

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.",

keywords = "direct reductive amination (DRA), molybdenum dioxide dichloride, phenylsilane, sodium triacetoxyborohydride, aryl PFP-sulfonate esters",

author = "Smith, \{Clive A.\} and Cross, \{Laura E.\} and Kimberley Hughes and Davis, \{Rebecca E.\} and Judd, \{Duncan B.\} and Merritt, \{Andrew T.\}",

year = "2009",

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day = "26",

doi = "10.1016/j.tetlet.2009.06.071",

language = "English",

volume = "50",

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journal = "Tetrahedron Letters",

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TY - JOUR

T1 - Direct reductive aminations with catalytic molybdenum dioxide dichloride and phenylsilane

AU - Smith, Clive A.

AU - Cross, Laura E.

AU - Hughes, Kimberley

AU - Davis, Rebecca E.

AU - Judd, Duncan B.

AU - Merritt, Andrew T.

PY - 2009/8/26

Y1 - 2009/8/26

N2 - 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.

AB - 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.

KW - direct reductive amination (DRA)

KW - molybdenum dioxide dichloride

KW - phenylsilane

KW - sodium triacetoxyborohydride

KW - aryl PFP-sulfonate esters

UR - http://dx.doi.org/10.1016/j.tetlet.2009.06.071

U2 - 10.1016/j.tetlet.2009.06.071

DO - 10.1016/j.tetlet.2009.06.071

M3 - Article

SN - 0040-4039

VL - 50

SP - 4906

EP - 4911

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 34

ER -

Direct reductive aminations with catalytic molybdenum dioxide dichloride and phenylsilane

Abstract

Keywords

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