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

Takehiko Matsumura, Masahisa Nakada

    Research output: Contribution to journalArticle

    13 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 languageEnglish
    Pages (from-to)1829-1834
    Number of pages6
    JournalTetrahedron Letters
    Volume55
    Issue number10
    DOIs
    Publication statusPublished - 2014 Mar 5

    Fingerprint

    Amination
    Bismuth
    Chlorides
    Lewis Acids
    Amines
    Costs and Cost Analysis
    triethylsilane
    Costs

    Keywords

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

    ASJC Scopus subject areas

    • Biochemistry
    • Organic Chemistry
    • Drug Discovery

    Cite this

    Direct reductive amination using triethylsilane and catalytic bismuth(III) chloride. / Matsumura, Takehiko; Nakada, Masahisa.

    In: Tetrahedron Letters, Vol. 55, No. 10, 05.03.2014, p. 1829-1834.

    Research output: Contribution to journalArticle

    @article{aa09311e2301430293959e5740bfb0d9,
    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",
    year = "2014",
    month = "3",
    day = "5",
    doi = "10.1016/j.tetlet.2014.01.132",
    language = "English",
    volume = "55",
    pages = "1829--1834",
    journal = "Tetrahedron Letters",
    issn = "0040-4039",
    publisher = "Elsevier Limited",
    number = "10",

    }

    TY - JOUR

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

    AU - Matsumura, Takehiko

    AU - Nakada, Masahisa

    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

    UR - http://www.scopus.com/inward/record.url?scp=84896718408&partnerID=8YFLogxK

    UR - http://www.scopus.com/inward/citedby.url?scp=84896718408&partnerID=8YFLogxK

    U2 - 10.1016/j.tetlet.2014.01.132

    DO - 10.1016/j.tetlet.2014.01.132

    M3 - Article

    AN - SCOPUS:84896718408

    VL - 55

    SP - 1829

    EP - 1834

    JO - Tetrahedron Letters

    JF - Tetrahedron Letters

    SN - 0040-4039

    IS - 10

    ER -