Zirconium-Catalyzed Reaction of 1-Alkynyl Sulfides with Et3Al: A Novel Route to Trisubstituted 1-Alkenyl Sulfides
Publication type: Journal Article
Publication date: 2018-06-21
scimago Q3
wos Q3
SJR: 0.437
CiteScore: 3.3
Impact factor: 1.4
ISSN: 09365214, 14372096
Organic Chemistry
Abstract
The reaction of 1-alkynyl sulfides and alkynyl sulfoxides with Et3Al under zirconocene catalysis conditions has been studied. The interaction between 1-alkynyl sulfides and Et3Al in the presence of catalytic amounts of Cp2ZrCl2 leads to trisubstituted 1-alkenyl sulfides in moderate to good yields (56–73%) with high regioselectivity and stereoselectivity. 1-Alkynyl sulfoxides, upon treatment with Et3Al under the same reaction conditions, undergoes reduction to give sulfides. The excess of Et3Al (7 equiv) in this reaction causes cyclic carboalumination of in situ generated 1-alkynyl sulfide to form trisubstituted 1-alkenyl sulfides in quantitative yield.
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Kadikova R. et al. Zirconium-Catalyzed Reaction of 1-Alkynyl Sulfides with Et3Al: A Novel Route to Trisubstituted 1-Alkenyl Sulfides // Synlett. 2018. Vol. 29. No. 13. pp. 1773-1775.
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Kadikova R., Ramazanov I., Vyatkin A., Dzhemilev U. Zirconium-Catalyzed Reaction of 1-Alkynyl Sulfides with Et3Al: A Novel Route to Trisubstituted 1-Alkenyl Sulfides // Synlett. 2018. Vol. 29. No. 13. pp. 1773-1775.
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TY - JOUR
DO - 10.1055/s-0037-1610431
UR - https://doi.org/10.1055/s-0037-1610431
TI - Zirconium-Catalyzed Reaction of 1-Alkynyl Sulfides with Et3Al: A Novel Route to Trisubstituted 1-Alkenyl Sulfides
T2 - Synlett
AU - Kadikova, Rita
AU - Ramazanov, Ilfir
AU - Vyatkin, Alexey
AU - Dzhemilev, Usein
PY - 2018
DA - 2018/06/21
PB - Georg Thieme Verlag KG
SP - 1773-1775
IS - 13
VL - 29
SN - 0936-5214
SN - 1437-2096
ER -
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@article{2018_Kadikova,
author = {Rita Kadikova and Ilfir Ramazanov and Alexey Vyatkin and Usein Dzhemilev},
title = {Zirconium-Catalyzed Reaction of 1-Alkynyl Sulfides with Et3Al: A Novel Route to Trisubstituted 1-Alkenyl Sulfides},
journal = {Synlett},
year = {2018},
volume = {29},
publisher = {Georg Thieme Verlag KG},
month = {jun},
url = {https://doi.org/10.1055/s-0037-1610431},
number = {13},
pages = {1773--1775},
doi = {10.1055/s-0037-1610431}
}
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Kadikova, Rita, et al. “Zirconium-Catalyzed Reaction of 1-Alkynyl Sulfides with Et3Al: A Novel Route to Trisubstituted 1-Alkenyl Sulfides.” Synlett, vol. 29, no. 13, Jun. 2018, pp. 1773-1775. https://doi.org/10.1055/s-0037-1610431.