Base-stabilized nitrilium ions as convenient imine synthons

Tom Van Dijk; Martijn S. Bakker; Flip Holtrop; Martin Nieger; J. Chris Slootweg; Koop Lammertsma

doi:10.1021/acs.orglett.5b00339

Base-stabilized nitrilium ions as convenient imine synthons

Tom Van Dijk, Martijn S. Bakker, Flip Holtrop, Martin Nieger, J. Chris Slootweg, Koop Lammertsma

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

20 Citations (Scopus)

Abstract

A simple and efficient methodology is presented for the synthesis of a wide range of substituted imines. It is based on stabilizing readily available, but thermally labile, N-alkylnitrilium triflates with pyridine or DMAP to moderately air-stable adducts. These base-stabilized imine synthons react conveniently with phosphorus- and nitrogen-based nucleophiles to amidines and phosphaamidines.

Original language	English
Pages (from-to)	1461-1464
Number of pages	4
Journal	Organic Letters
Volume	17
Issue number	6
DOIs	https://doi.org/10.1021/acs.orglett.5b00339
Publication status	Published - 20 Mar 2015
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "A simple and efficient methodology is presented for the synthesis of a wide range of substituted imines. It is based on stabilizing readily available, but thermally labile, N-alkylnitrilium triflates with pyridine or DMAP to moderately air-stable adducts. These base-stabilized imine synthons react conveniently with phosphorus- and nitrogen-based nucleophiles to amidines and phosphaamidines.",

author = "{Van Dijk}, Tom and Bakker, {Martijn S.} and Flip Holtrop and Martin Nieger and Slootweg, {J. Chris} and Koop Lammertsma",

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T1 - Base-stabilized nitrilium ions as convenient imine synthons

AU - Van Dijk, Tom

AU - Bakker, Martijn S.

AU - Holtrop, Flip

AU - Nieger, Martin

AU - Slootweg, J. Chris

AU - Lammertsma, Koop

PY - 2015/3/20

Y1 - 2015/3/20

N2 - A simple and efficient methodology is presented for the synthesis of a wide range of substituted imines. It is based on stabilizing readily available, but thermally labile, N-alkylnitrilium triflates with pyridine or DMAP to moderately air-stable adducts. These base-stabilized imine synthons react conveniently with phosphorus- and nitrogen-based nucleophiles to amidines and phosphaamidines.

AB - A simple and efficient methodology is presented for the synthesis of a wide range of substituted imines. It is based on stabilizing readily available, but thermally labile, N-alkylnitrilium triflates with pyridine or DMAP to moderately air-stable adducts. These base-stabilized imine synthons react conveniently with phosphorus- and nitrogen-based nucleophiles to amidines and phosphaamidines.

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DO - 10.1021/acs.orglett.5b00339

M3 - Article

AN - SCOPUS:84925379386

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SP - 1461

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JO - Organic Letters

JF - Organic Letters

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ER -

Base-stabilized nitrilium ions as convenient imine synthons

Abstract

ASJC Scopus subject areas

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