One-pot oxidative amidation of aldehydes via the generation of nitrile imine intermediates

Martyn C. Henry; Laura Minty; Alexander C. W. Kwok; Jessica M. L. Elwood; Adam J. Foulis; Jonathan  Pettinger; Craig Jamieson

doi:10.1021/acs.joc.4c00575

One-pot oxidative amidation of aldehydes via the generation of nitrile imine intermediates

Martyn C. Henry, Laura Minty, Alexander C. W. Kwok, Jessica M. L. Elwood, Adam J. Foulis, Jonathan Pettinger, Craig Jamieson

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

5 Downloads (Pure)

Abstract

A one-pot procedure for the oxidative amidation of aldehydes via the in situ generation of reactive nitrile imine (NI) intermediates has been developed. Distinct from our progenitor processes, mechanistic and control experiments revealed that the NI undergoes rapid oxidation to an acyl diazene species, which then facilitates N-acylation of an amine. A range of substrates have been explored, including application in the synthesis of pharmaceutically relevant compounds.

Original language	English
Pages (from-to)	7913-7926
Number of pages	14
Journal	Journal of Organic Chemistry
Volume	89
Issue number	11
Early online date	23 May 2024
DOIs	https://doi.org/10.1021/acs.joc.4c00575
Publication status	Published - 7 Jun 2024

Keywords

one-pot
oxidative amidation
aldehydes
nitrile imine (NI)
amines
oxidation
synthesis
pharmaceutical applications

Access to Document

10.1021/acs.joc.4c00575

Henry-etal-JOC-2024-One-pot-oxidative-amidation-of-aldehydes-via-the-generation-ofFinal published version, 3.3 MBLicence: CC BY 4.0

Cite this

@article{57b2a62a1fe942188fb3907afda56db1,

title = "One-pot oxidative amidation of aldehydes via the generation of nitrile imine intermediates",

abstract = "A one-pot procedure for the oxidative amidation of aldehydes via the in situ generation of reactive nitrile imine (NI) intermediates has been developed. Distinct from our progenitor processes, mechanistic and control experiments revealed that the NI undergoes rapid oxidation to an acyl diazene species, which then facilitates N-acylation of an amine. A range of substrates have been explored, including application in the synthesis of pharmaceutically relevant compounds. ",

keywords = "one-pot, oxidative amidation, aldehydes, nitrile imine (NI), amines, oxidation, synthesis, pharmaceutical applications",

author = "Henry, {Martyn C.} and Laura Minty and Kwok, {Alexander C. W.} and Elwood, {Jessica M. L.} and Foulis, {Adam J.} and Jonathan Pettinger and Craig Jamieson",

year = "2024",

month = jun,

day = "7",

doi = "10.1021/acs.joc.4c00575",

language = "English",

volume = "89",

pages = "7913--7926",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "11",

}

TY - JOUR

T1 - One-pot oxidative amidation of aldehydes via the generation of nitrile imine intermediates

AU - Henry, Martyn C.

AU - Minty, Laura

AU - Kwok, Alexander C. W.

AU - Elwood, Jessica M. L.

AU - Foulis, Adam J.

AU - Pettinger, Jonathan

AU - Jamieson, Craig

PY - 2024/6/7

Y1 - 2024/6/7

N2 - A one-pot procedure for the oxidative amidation of aldehydes via the in situ generation of reactive nitrile imine (NI) intermediates has been developed. Distinct from our progenitor processes, mechanistic and control experiments revealed that the NI undergoes rapid oxidation to an acyl diazene species, which then facilitates N-acylation of an amine. A range of substrates have been explored, including application in the synthesis of pharmaceutically relevant compounds.

AB - A one-pot procedure for the oxidative amidation of aldehydes via the in situ generation of reactive nitrile imine (NI) intermediates has been developed. Distinct from our progenitor processes, mechanistic and control experiments revealed that the NI undergoes rapid oxidation to an acyl diazene species, which then facilitates N-acylation of an amine. A range of substrates have been explored, including application in the synthesis of pharmaceutically relevant compounds.

KW - one-pot

KW - oxidative amidation

KW - aldehydes

KW - nitrile imine (NI)

KW - amines

KW - oxidation

KW - synthesis

KW - pharmaceutical applications

UR - https://pubs.acs.org/journal/joceah

U2 - 10.1021/acs.joc.4c00575

DO - 10.1021/acs.joc.4c00575

M3 - Article

SN - 0022-3263

VL - 89

SP - 7913

EP - 7926

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 11

ER -

One-pot oxidative amidation of aldehydes via the generation of nitrile imine intermediates

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Industrial CASE Account - University of Strathclyde 2021

Cite this

One-pot oxidative amidation of aldehydes via the generation of nitrile imine intermediates

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Projects

Industrial CASE Account - University of Strathclyde 2021

Cite this