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Keywords = 2-zincoethylzincation

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4 pages, 667 KiB  
Proceeding Paper
Ti(O-iPr)4-EtMgBr-Catalyzed Reaction of Dialkyl-Substituted Alkynes with Et2Zn
by Azat M. Gabdullin, Oleg S. Mozgovoj, Rita N. Kadikova, Ilfir R. Ramazanov and Usein M. Dzhemilev
Chem. Proc. 2022, 8(1), 61; https://doi.org/10.3390/ecsoc-25-11639 - 12 Nov 2021
Viewed by 1800
Abstract
For the first time, the Ti(O-iPr)4-EtMgBr carbozincation of dialkyl-substituted alkynes with Et2Zn was carried out. It was found that the reaction of 1,2-disubstituted alkynes (5-decyne, 4-octyne, 3-hexyne) with Et2Zn is accompanied by the regioselective formation [...] Read more.
For the first time, the Ti(O-iPr)4-EtMgBr carbozincation of dialkyl-substituted alkynes with Et2Zn was carried out. It was found that the reaction of 1,2-disubstituted alkynes (5-decyne, 4-octyne, 3-hexyne) with Et2Zn is accompanied by the regioselective formation of stereoisomeric tetra-alkyl-substituted hexa-1,3-diene derivatives in high yield. It was also found that the 2-zincoethylzincation of dialkyl-substituted alkynes in the presence of catalytic amounts of Ti(O-iPr)4 and EtMgBr does not stop at the stage of ethylzincation of the triple bond, but is accompanied by the involvement of a second alkyne molecule with the formation of two stereoisomeric hexa-1,3-diene derivatives. The effect of the solvent on the carbozincation of the dilkyl-substituted alkynes under the conditions of titanium-magnesium catalysis was studied. Full article
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11 pages, 1643 KiB  
Communication
Carbozincation of Substituted 2-Alkynylamines, 1-Alkynylphosphines, 1-Alkynylphosphine Sulfides with Et2Zn in the Presence of Catalytic System of Ti(O-iPr)4 and EtMgBr
by Rita N. Kadikova, Ilfir R. Ramazanov, Azat M. Gabdullin, Oleg S. Mozgovoi and Usein M. Dzhemilev
Catalysts 2019, 9(12), 1022; https://doi.org/10.3390/catal9121022 - 4 Dec 2019
Cited by 10 | Viewed by 3468
Abstract
The EtMgBr and Ti(O-iPr)4-catalyzed ethylzincation of 1-alkynylphosphine sulfides with Et2Zn in diethyl ether followed by hydrolysis and deuterolysis affords corresponding β,β-disubstituted 1-alkenylphosphine sulfides with high yield. The EtMgBr and Ti(O-iPr)4-catalyzed [...] Read more.
The EtMgBr and Ti(O-iPr)4-catalyzed ethylzincation of 1-alkynylphosphine sulfides with Et2Zn in diethyl ether followed by hydrolysis and deuterolysis affords corresponding β,β-disubstituted 1-alkenylphosphine sulfides with high yield. The EtMgBr and Ti(O-iPr)4-catalyzed reaction of 2-alkynylamines, 1-alkynylphosphines, and 1-alkenylphosphine sulfides with Et2Zn in various solvents was studied. It has been found that the reaction of 2-alkynylamines and 1-alkynylphosphines in methylene chloride, hexane, toluene, benzene, and anisole leads to the selective formation of 2-alkenylamines and 1-alkenylphosphine oxides after oxidation with H2O2. Full article
(This article belongs to the Special Issue Metal-Based Catalysts in Organic Synthesis)
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