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

Agnieszka Adamczyk-Woźniak , Raluca M. Fratila , Izabela Madura , Alicja Pawełko , Andrzej Sporzyński , Marta Tumanowicz , Aldrik H. Velders , Jacek Żyła

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.
Author Agnieszka Adamczyk-Woźniak (FC / DPC)
Agnieszka Adamczyk-Woźniak,,
- Department Of Physical Chemistry
, Raluca M. Fratila - [University of Twente]
Raluca M. Fratila,,
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, Izabela Madura (FC / CICSST)
Izabela Madura,,
- Chair Of Inorganic Chemistry And Solid State Technology
, Alicja Pawełko - [Politechnika Warszawska]
Alicja Pawełko,,
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, Andrzej Sporzyński (FC / DPC)
Andrzej Sporzyński,,
- Department Of Physical Chemistry
, Marta Tumanowicz - [Warsaw University of Technology (PW), MNiSW [80]]
Marta Tumanowicz,,
-
- Politechnika Warszawska
, Aldrik H. Velders - [University of Twente]
Aldrik H. Velders,,
-
-
, Jacek Żyła
Jacek Żyła,,
-
Journal seriesTetrahedron Letters, ISSN 0040-4039, (A 30 pkt)
Issue year2011
Vol52
No49
Pages6639-6642
Keywords in EnglishAmination–reduction, Aromatic secondary amines, benzoxaborole, Boronic acids
ASJC Classification1605 Organic Chemistry; 3002 Drug Discovery; 1303 Biochemistry
DOIDOI:10.1016/j.tetlet.2011.10.008
URL http://www.sciencedirect.com/science/article/pii/S0040403911017163
Languageen angielski
File
1-s2.0-S0040403911017163-main.pdf 366.96 KB
Score (nominal)30
Score sourcejournalList
Publication indicators Scopus Citations = 16; WoS Citations = 12; Scopus SNIP (Source Normalised Impact per Paper): 2014 = 0.796; WoS Impact Factor: 2011 = 2.683 (2) - 2011=2.588 (5)
Citation count*11 (2016-06-01)
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