Reactivity of 2-formylphenylboronic acid toward secondary aromatic amines in amination–reduction reactions

Agnieszka Adamczyk-Wozniak; R.M. Fratila; Izabela D. Madura; Alicja Pawelko; Andrzej Sporzynski; Marta Tumanowicz; Aldrik Velders; Jacek Zyla

doi:10.1016/j.tetlet.2011.10.008

Reactivity of 2-formylphenylboronic acid toward secondary aromatic amines in amination–reduction reactions

Agnieszka Adamczyk-Wozniak, R.M. Fratila, Izabela D. Madura, Alicja Pawelko, Andrzej Sporzynski, Marta Tumanowicz, Aldrik Velders, Jacek Zyla

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Abstract

The synthesis of 2-(arylaminomethyl)phenylboronic acid via an amination–reduction reaction has been investigated within a model system comprising 2-formylphenylboronic acid and N-ethylaniline. Adoption of the appropriate reaction conditions influences the reactivity of 2-formylphenylboronic acid, enabling efficient synthesis of so-far unobtainable 2-(arylaminomethyl)phenylboronic compounds. The first crystal structure of the aromatic amine derivative has been determined and described.

Original language	English
Pages (from-to)	6639-6642
Journal	Tetrahedron letters
Volume	52
Issue number	49
DOIs	https://doi.org/10.1016/j.tetlet.2011.10.008
Publication status	Published - 2011

Keywords

IR-104361
METIS-283621

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10.1016/j.tetlet.2011.10.008

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title = "Reactivity of 2-formylphenylboronic acid toward secondary aromatic amines in amination–reduction reactions",

abstract = "The synthesis of 2-(arylaminomethyl)phenylboronic acid via an amination–reduction reaction has been investigated within a model system comprising 2-formylphenylboronic acid and N-ethylaniline. Adoption of the appropriate reaction conditions influences the reactivity of 2-formylphenylboronic acid, enabling efficient synthesis of so-far unobtainable 2-(arylaminomethyl)phenylboronic compounds. The first crystal structure of the aromatic amine derivative has been determined and described.",

keywords = "IR-104361, METIS-283621",

author = "Agnieszka Adamczyk-Wozniak and R.M. Fratila and Madura, {Izabela D.} and Alicja Pawelko and Andrzej Sporzynski and Marta Tumanowicz and Aldrik Velders and Jacek Zyla",

year = "2011",

doi = "10.1016/j.tetlet.2011.10.008",

language = "English",

volume = "52",

pages = "6639--6642",

journal = "Tetrahedron letters",

issn = "0040-4039",

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TY - JOUR

T1 - Reactivity of 2-formylphenylboronic acid toward secondary aromatic amines in amination–reduction reactions

AU - Adamczyk-Wozniak, Agnieszka

AU - Fratila, R.M.

AU - Madura, Izabela D.

AU - Pawelko, Alicja

AU - Sporzynski, Andrzej

AU - Tumanowicz, Marta

AU - Velders, Aldrik

AU - Zyla, Jacek

PY - 2011

Y1 - 2011

N2 - The synthesis of 2-(arylaminomethyl)phenylboronic acid via an amination–reduction reaction has been investigated within a model system comprising 2-formylphenylboronic acid and N-ethylaniline. Adoption of the appropriate reaction conditions influences the reactivity of 2-formylphenylboronic acid, enabling efficient synthesis of so-far unobtainable 2-(arylaminomethyl)phenylboronic compounds. The first crystal structure of the aromatic amine derivative has been determined and described.

AB - The synthesis of 2-(arylaminomethyl)phenylboronic acid via an amination–reduction reaction has been investigated within a model system comprising 2-formylphenylboronic acid and N-ethylaniline. Adoption of the appropriate reaction conditions influences the reactivity of 2-formylphenylboronic acid, enabling efficient synthesis of so-far unobtainable 2-(arylaminomethyl)phenylboronic compounds. The first crystal structure of the aromatic amine derivative has been determined and described.

KW - IR-104361

KW - METIS-283621

U2 - 10.1016/j.tetlet.2011.10.008

DO - 10.1016/j.tetlet.2011.10.008

M3 - Article

SN - 0040-4039

VL - 52

SP - 6639

EP - 6642

JO - Tetrahedron letters

JF - Tetrahedron letters

IS - 49

ER -

Reactivity of 2-formylphenylboronic acid toward secondary aromatic amines in amination–reduction reactions

Abstract

Keywords

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