Carbene insertion to N-H bonds of 2-aminothiazole and 2-amino-1,3,4-thiadiazole derivatives catalyzed by iron phthalocyanine
1
Publication type: Journal Article
Publication date: 2019-04-01
scimago Q3
wos Q4
SJR: 0.228
CiteScore: 1.8
Impact factor: 0.9
ISSN: 10884246, 10991409
General Chemistry
Abstract
Iron(III) phthalocyaninate decorated with crown ether substituents, [(15C5)4PcFe]Cl, efficiently catalyzed the insertion of carbene derived from ethyl diazoacetate to six amines functionalized with thiazole, thiazoline and thiadiazole heterocycles. The reactions were carried out under practical conditions using EDA:amine stoechiometric ratio with 0.05 mol% catalyst loading. Turnover numbers up to 3360 have been achieved. The aminoacid derivatives bearing heterocyclic moieties were obtained under catalytic conditions for the first time with 36–69% yields in the case of single N–H insertion products and up to 77% in the case of double N–H insertion products.
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Cailler L. P. et al. Carbene insertion to N-H bonds of 2-aminothiazole and 2-amino-1,3,4-thiadiazole derivatives catalyzed by iron phthalocyanine // Journal of Porphyrins and Phthalocyanines. 2019. Vol. 23. No. 4-5. pp. 497-506.
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Cailler L. P., Sorokin P. B., Martynov A. G., Gorbunova Y. G., Tsivadze A. Y., Sorokin A. B. Carbene insertion to N-H bonds of 2-aminothiazole and 2-amino-1,3,4-thiadiazole derivatives catalyzed by iron phthalocyanine // Journal of Porphyrins and Phthalocyanines. 2019. Vol. 23. No. 4-5. pp. 497-506.
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TY - JOUR
DO - 10.1142/S1088424619500354
UR - https://www.worldscientific.com/doi/abs/10.1142/S1088424619500354
TI - Carbene insertion to N-H bonds of 2-aminothiazole and 2-amino-1,3,4-thiadiazole derivatives catalyzed by iron phthalocyanine
T2 - Journal of Porphyrins and Phthalocyanines
AU - Cailler, Lucie P.
AU - Sorokin, Pavel B.
AU - Martynov, Alexander G.
AU - Gorbunova, Yulia G.
AU - Tsivadze, Aslan Yu.
AU - Sorokin, Alexander B.
PY - 2019
DA - 2019/04/01
PB - World Scientific
SP - 497-506
IS - 4-5
VL - 23
SN - 1088-4246
SN - 1099-1409
ER -
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@article{2019_Cailler,
author = {Lucie P. Cailler and Pavel B. Sorokin and Alexander G. Martynov and Yulia G. Gorbunova and Aslan Yu. Tsivadze and Alexander B. Sorokin},
title = {Carbene insertion to N-H bonds of 2-aminothiazole and 2-amino-1,3,4-thiadiazole derivatives catalyzed by iron phthalocyanine},
journal = {Journal of Porphyrins and Phthalocyanines},
year = {2019},
volume = {23},
publisher = {World Scientific},
month = {apr},
url = {https://www.worldscientific.com/doi/abs/10.1142/S1088424619500354},
number = {4-5},
pages = {497--506},
doi = {10.1142/S1088424619500354}
}
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Cailler, Lucie P., et al. “Carbene insertion to N-H bonds of 2-aminothiazole and 2-amino-1,3,4-thiadiazole derivatives catalyzed by iron phthalocyanine.” Journal of Porphyrins and Phthalocyanines, vol. 23, no. 4-5, Apr. 2019, pp. 497-506. https://www.worldscientific.com/doi/abs/10.1142/S1088424619500354.