Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование
Isoxazole Strategy for the Synthesis of 2,2′-Bipyridine Ligands : Symmetrical and Unsymmetrical 6,6′-Binicotinates, 2,2′-Bipyridine-5-carboxylates, and Their Metal Complexes. / Galenko, Ekaterina E.; Novikov, Mikhail S.; Shakirova, Firuza M.; Shakirova, Julia R.; Kornyakov, Ilya V.; Bodunov, Vladimir A.; Khlebnikov, Alexander F.
в: Journal of Organic Chemistry, Том 84, № 6, 15.03.2019, стр. 3524-3536.Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование
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TY - JOUR
T1 - Isoxazole Strategy for the Synthesis of 2,2′-Bipyridine Ligands
T2 - Symmetrical and Unsymmetrical 6,6′-Binicotinates, 2,2′-Bipyridine-5-carboxylates, and Their Metal Complexes
AU - Galenko, Ekaterina E.
AU - Novikov, Mikhail S.
AU - Shakirova, Firuza M.
AU - Shakirova, Julia R.
AU - Kornyakov, Ilya V.
AU - Bodunov, Vladimir A.
AU - Khlebnikov, Alexander F.
PY - 2019/3/15
Y1 - 2019/3/15
N2 - An effective strategy was developed for the synthesis of new 2,2′-bipyridine ligands, symmetrical and unsymmetrical 6,6′-binicotinates, and 2,2′-bipyridine-5-carboxylates, from 4-propargylisoxazoles. The synthesis of symmetrical 2,2′-disubstituted 6,6′-binicotinates was achieved using the Eglinton reaction of 5-methoxy-4-(prop-2-yn-1-yl)isoxazoles with Cu(OAc) 2 , followed by Fe(NTf 2 ) 2 /Au(NTf 2 )tBuXPhos-catalyzed isomerization of the so-formed mixture of isoxazole/azirine-substituted biacetylenic intermediates. Unsymmetrical 2,2′-disubstituted 6,6′-binicotinates were prepared via a copper-free Sonogashira coupling of 5-methoxy-4-(prop-2-yn-1-yl)isoxazoles with 6-bromonicotinates to give methyl 6-(3-(5-methoxyisoxazol-4-yl)prop-1-ynyl)pyridine-3-carboxylates, followed by a transformation of the propargylisoxazole moiety of the adduct into the pyridine fragment under Fe(II)/Au(I) relay catalysis conditions. 6-(Pyrid-2-yl)nicotinates were synthesized by a Stille-type coupling of 2-(tributylstannyl)pyridine with 6-bromonicotinates. Several cyclopalladated complexes of a new series of 6,6′-binicotinates and 2,2′-bipyridine-5-carboxylates and the homoleptic Cu(I) complex were synthesized in high yields.
AB - An effective strategy was developed for the synthesis of new 2,2′-bipyridine ligands, symmetrical and unsymmetrical 6,6′-binicotinates, and 2,2′-bipyridine-5-carboxylates, from 4-propargylisoxazoles. The synthesis of symmetrical 2,2′-disubstituted 6,6′-binicotinates was achieved using the Eglinton reaction of 5-methoxy-4-(prop-2-yn-1-yl)isoxazoles with Cu(OAc) 2 , followed by Fe(NTf 2 ) 2 /Au(NTf 2 )tBuXPhos-catalyzed isomerization of the so-formed mixture of isoxazole/azirine-substituted biacetylenic intermediates. Unsymmetrical 2,2′-disubstituted 6,6′-binicotinates were prepared via a copper-free Sonogashira coupling of 5-methoxy-4-(prop-2-yn-1-yl)isoxazoles with 6-bromonicotinates to give methyl 6-(3-(5-methoxyisoxazol-4-yl)prop-1-ynyl)pyridine-3-carboxylates, followed by a transformation of the propargylisoxazole moiety of the adduct into the pyridine fragment under Fe(II)/Au(I) relay catalysis conditions. 6-(Pyrid-2-yl)nicotinates were synthesized by a Stille-type coupling of 2-(tributylstannyl)pyridine with 6-bromonicotinates. Several cyclopalladated complexes of a new series of 6,6′-binicotinates and 2,2′-bipyridine-5-carboxylates and the homoleptic Cu(I) complex were synthesized in high yields.
KW - ORGANIC FRAMEWORKS
KW - FLUORESCENT-PROBE
KW - ISOMERIZATION
KW - BIPYRIDINE
KW - MOLECULES
UR - http://www.scopus.com/inward/record.url?scp=85062856056&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.9b00115
DO - 10.1021/acs.joc.9b00115
M3 - Article
C2 - 30810032
AN - SCOPUS:85062856056
VL - 84
SP - 3524
EP - 3536
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 6
ER -
ID: 39828832