Oxoammonium salt-mediated oxidative nitriles synthesis from aldehydes with ammonium acetate

Myeong Jin Kim; Junyoung Mun; Jinho Kim

doi:10.1016/j.tetlet.2017.11.002

Oxoammonium salt-mediated oxidative nitriles synthesis from aldehydes with ammonium acetate

Myeong Jin Kim
, Junyoung Mun
, Jinho Kim

Incheon National University

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

13 Scopus citations

Abstract

An efficient and scalable route for the synthesis of nitriles was developed by oxoammonium salt (4-acetamido-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate) mediated oxidative conversion of aldehydes with NH₄OAc. A variety of aliphatic aldehydes as well as benzaldehydes were converted into the corresponding nitriles in high yields. The nitroxyl radical which is the reduced species of the used oxoammonium salt was recovered by simple acid-base extraction for the recycling.

Original language	English
Pages (from-to)	4695-4698
Number of pages	4
Journal	Tetrahedron Letters
Volume	58
Issue number	50
DOIs	https://doi.org/10.1016/j.tetlet.2017.11.002
State	Published - 13 Dec 2017
Externally published	Yes

Keywords

Ammonium acetate
Nitriles
Organic synthesis
Oxidation
Oxoammonium salt

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10.1016/j.tetlet.2017.11.002

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title = "Oxoammonium salt-mediated oxidative nitriles synthesis from aldehydes with ammonium acetate",

abstract = "An efficient and scalable route for the synthesis of nitriles was developed by oxoammonium salt (4-acetamido-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate) mediated oxidative conversion of aldehydes with NH4OAc. A variety of aliphatic aldehydes as well as benzaldehydes were converted into the corresponding nitriles in high yields. The nitroxyl radical which is the reduced species of the used oxoammonium salt was recovered by simple acid-base extraction for the recycling.",

keywords = "Ammonium acetate, Nitriles, Organic synthesis, Oxidation, Oxoammonium salt",

author = "Kim, \{Myeong Jin\} and Junyoung Mun and Jinho Kim",

note = "Publisher Copyright: {\textcopyright} 2017 Elsevier Ltd",

year = "2017",

month = dec,

day = "13",

doi = "10.1016/j.tetlet.2017.11.002",

language = "English",

volume = "58",

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journal = "Tetrahedron Letters",

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T1 - Oxoammonium salt-mediated oxidative nitriles synthesis from aldehydes with ammonium acetate

AU - Kim, Myeong Jin

AU - Mun, Junyoung

AU - Kim, Jinho

PY - 2017/12/13

Y1 - 2017/12/13

N2 - An efficient and scalable route for the synthesis of nitriles was developed by oxoammonium salt (4-acetamido-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate) mediated oxidative conversion of aldehydes with NH4OAc. A variety of aliphatic aldehydes as well as benzaldehydes were converted into the corresponding nitriles in high yields. The nitroxyl radical which is the reduced species of the used oxoammonium salt was recovered by simple acid-base extraction for the recycling.

AB - An efficient and scalable route for the synthesis of nitriles was developed by oxoammonium salt (4-acetamido-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate) mediated oxidative conversion of aldehydes with NH4OAc. A variety of aliphatic aldehydes as well as benzaldehydes were converted into the corresponding nitriles in high yields. The nitroxyl radical which is the reduced species of the used oxoammonium salt was recovered by simple acid-base extraction for the recycling.

KW - Ammonium acetate

KW - Nitriles

KW - Organic synthesis

KW - Oxidation

KW - Oxoammonium salt

UR - https://www.scopus.com/pages/publications/85033582301

U2 - 10.1016/j.tetlet.2017.11.002

DO - 10.1016/j.tetlet.2017.11.002

M3 - Article

AN - SCOPUS:85033582301

SN - 0040-4039

VL - 58

SP - 4695

EP - 4698

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 50

ER -

Oxoammonium salt-mediated oxidative nitriles synthesis from aldehydes with ammonium acetate

Abstract

Keywords

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