Highly Selective Carboxylative Cyclization of Allenylmethylamines with Carbon Dioxide Using N-Heterocyclic Carbene-Silver(I) Catalysts
Тип публикации: Journal Article
Дата публикации: 2015-04-28
SCImago Q1
Tоп 10% SCImago
WOS Q1
БС1
SJR: 1.007
CiteScore: 7.7
Impact factor: 4.7
ISSN: 15237060, 15237052
PubMed ID:
25918943
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Краткое описание
Silver(I) carboxylate complexes promote the carboxylative cyclization of allenylmethylamines to afford 5-alkenyl-1,3-oxazolidin-2-ones in 2-propanol. The use of an N-heterocyclic carbene ligand (IPr) under pressurized CO2 is effective in suppressing the intramolecular hydroamination that leads to 2,5-dihydropyrroles. The mechanism involving a nucleophilic attack of the carbamate of the allene moiety and a subsequent protonation was realized on the basis of experimental and theoretical results involving a model intermediate, the alkenylgold(I) complex, which was synthesized from Au(OH)(IPr) and 1-methylamino-2,3-butadiene.
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ГОСТ
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Yamashita K. et al. Highly Selective Carboxylative Cyclization of Allenylmethylamines with Carbon Dioxide Using N-Heterocyclic Carbene-Silver(I) Catalysts // Organic Letters. 2015. Vol. 17. No. 10. pp. 2334-2337.
ГОСТ со всеми авторами (до 50)
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Yamashita K., Hase S., Kayaki Y., Ikariya T. Highly Selective Carboxylative Cyclization of Allenylmethylamines with Carbon Dioxide Using N-Heterocyclic Carbene-Silver(I) Catalysts // Organic Letters. 2015. Vol. 17. No. 10. pp. 2334-2337.
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TY - JOUR
DO - 10.1021/acs.orglett.5b00809
UR - https://doi.org/10.1021/acs.orglett.5b00809
TI - Highly Selective Carboxylative Cyclization of Allenylmethylamines with Carbon Dioxide Using N-Heterocyclic Carbene-Silver(I) Catalysts
T2 - Organic Letters
AU - Yamashita, Kyohei
AU - Hase, Shun
AU - Kayaki, Yoshihito
AU - Ikariya, Takao
PY - 2015
DA - 2015/04/28
PB - American Chemical Society (ACS)
SP - 2334-2337
IS - 10
VL - 17
PMID - 25918943
SN - 1523-7060
SN - 1523-7052
ER -
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BibTex (до 50 авторов)
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@article{2015_Yamashita,
author = {Kyohei Yamashita and Shun Hase and Yoshihito Kayaki and Takao Ikariya},
title = {Highly Selective Carboxylative Cyclization of Allenylmethylamines with Carbon Dioxide Using N-Heterocyclic Carbene-Silver(I) Catalysts},
journal = {Organic Letters},
year = {2015},
volume = {17},
publisher = {American Chemical Society (ACS)},
month = {apr},
url = {https://doi.org/10.1021/acs.orglett.5b00809},
number = {10},
pages = {2334--2337},
doi = {10.1021/acs.orglett.5b00809}
}
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MLA
Скопировать
Yamashita, Kyohei, et al. “Highly Selective Carboxylative Cyclization of Allenylmethylamines with Carbon Dioxide Using N-Heterocyclic Carbene-Silver(I) Catalysts.” Organic Letters, vol. 17, no. 10, Apr. 2015, pp. 2334-2337. https://doi.org/10.1021/acs.orglett.5b00809.
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