Direct reductive amination using triethylsilane and catalytic bismuth(III) chloride

Takehiko Matsumura; Masahisa Nakada

doi:10.1016/j.tetlet.2014.01.132

Direct reductive amination using triethylsilane and catalytic bismuth(III) chloride

Takehiko Matsumura, Masahisa Nakada^*

^*Corresponding author for this work

School of Advanced Science and Engineering

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

15 Citations (Scopus)

Abstract

Direct reductive amination (DRA) using triethylsilane (TESH) and catalytic bismuth(III) chloride (BiCl₃) is described for the first time. The use of TESH and BiCl₃ provides easy handling, low cost, non-toxicity, and a mild Lewis acid activity, thereby meeting the demand for green and sustainable chemistry. The developed DRA is highly chemoselective and applicable to less-basic amines. The experimental results of this study revealed that the developed DRA could be catalyzed by BiCl₃, which was gradually reduced to Bi(0) or bismuth with a low valency by TESH, but TESCl, Bi(0), and Bi(0) with TESCl catalyzed the DRA to some extent.

Original language	English
Pages (from-to)	1829-1834
Number of pages	6
Journal	Tetrahedron Letters
Volume	55
Issue number	10
DOIs	https://doi.org/10.1016/j.tetlet.2014.01.132
Publication status	Published - 2014 Mar 5

Keywords

Bismuth(0)
Bismuth(III) chloride
Catalysis
Direct reductive amination
Triethylsilane

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2014.01.132

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title = "Direct reductive amination using triethylsilane and catalytic bismuth(III) chloride",

abstract = "Direct reductive amination (DRA) using triethylsilane (TESH) and catalytic bismuth(III) chloride (BiCl3) is described for the first time. The use of TESH and BiCl3 provides easy handling, low cost, non-toxicity, and a mild Lewis acid activity, thereby meeting the demand for green and sustainable chemistry. The developed DRA is highly chemoselective and applicable to less-basic amines. The experimental results of this study revealed that the developed DRA could be catalyzed by BiCl3, which was gradually reduced to Bi(0) or bismuth with a low valency by TESH, but TESCl, Bi(0), and Bi(0) with TESCl catalyzed the DRA to some extent.",

keywords = "Bismuth(0), Bismuth(III) chloride, Catalysis, Direct reductive amination, Triethylsilane",

author = "Takehiko Matsumura and Masahisa Nakada",

note = "Funding Information: This work was financially supported in part by Waseda University Grant for Special Research Projects, The Grant-in-Aid for Scientific Research on Innovative Areas {\textquoteleft}Organic Synthesis based on Reaction Integration, Development of New Methods and Creation of New Substances{\textquoteright} (No. 2105 ), Grant for Scientific Research (B) ( 25293003 ), and Grants for Excellent Graduate Schools (Practical Chemical Wisdom), MEXT, Japan . ",

year = "2014",

month = mar,

day = "5",

doi = "10.1016/j.tetlet.2014.01.132",

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T1 - Direct reductive amination using triethylsilane and catalytic bismuth(III) chloride

AU - Matsumura, Takehiko

AU - Nakada, Masahisa

N1 - Funding Information: This work was financially supported in part by Waseda University Grant for Special Research Projects, The Grant-in-Aid for Scientific Research on Innovative Areas ‘Organic Synthesis based on Reaction Integration, Development of New Methods and Creation of New Substances’ (No. 2105 ), Grant for Scientific Research (B) ( 25293003 ), and Grants for Excellent Graduate Schools (Practical Chemical Wisdom), MEXT, Japan .

PY - 2014/3/5

Y1 - 2014/3/5

N2 - Direct reductive amination (DRA) using triethylsilane (TESH) and catalytic bismuth(III) chloride (BiCl3) is described for the first time. The use of TESH and BiCl3 provides easy handling, low cost, non-toxicity, and a mild Lewis acid activity, thereby meeting the demand for green and sustainable chemistry. The developed DRA is highly chemoselective and applicable to less-basic amines. The experimental results of this study revealed that the developed DRA could be catalyzed by BiCl3, which was gradually reduced to Bi(0) or bismuth with a low valency by TESH, but TESCl, Bi(0), and Bi(0) with TESCl catalyzed the DRA to some extent.

AB - Direct reductive amination (DRA) using triethylsilane (TESH) and catalytic bismuth(III) chloride (BiCl3) is described for the first time. The use of TESH and BiCl3 provides easy handling, low cost, non-toxicity, and a mild Lewis acid activity, thereby meeting the demand for green and sustainable chemistry. The developed DRA is highly chemoselective and applicable to less-basic amines. The experimental results of this study revealed that the developed DRA could be catalyzed by BiCl3, which was gradually reduced to Bi(0) or bismuth with a low valency by TESH, but TESCl, Bi(0), and Bi(0) with TESCl catalyzed the DRA to some extent.

KW - Bismuth(0)

KW - Bismuth(III) chloride

KW - Catalysis

KW - Direct reductive amination

KW - Triethylsilane

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DO - 10.1016/j.tetlet.2014.01.132

M3 - Article

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 10

ER -

Direct reductive amination using triethylsilane and catalytic bismuth(III) chloride

Abstract

Keywords

ASJC Scopus subject areas

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