Cp2ZrCl2-EtMgBr-Catalysed Reaction of 2-Zincoethylzincation of 2-Alkynylamines

A. M. Gabdullin; Габдуллин А. М.; R. N. Kadikova; Кадикова Р. Н.; I. R. Ramazanov; Рамазанов И. Р.

doi:10.31857/S0514749224010056

Cp2ZrCl2-EtMgBr-Catalysed Reaction of 2-Zincoethylzincation of 2-Alkynylamines

Autores: Gabdullin A.M.¹, Kadikova R.N.¹, Ramazanov I.R.¹
Afiliações:
1. Institute of Petrochemistry and Catalysis, Ufa Federal Research Center, Russian Academy of Sciences
Edição: Volume 60, Nº 1 (2024)
Páginas: 68-74
Seção: Articles
URL: https://freezetech.ru/0514-7492/article/view/672226
DOI: https://doi.org/10.31857/S0514749224010056
EDN: https://elibrary.ru/ENKQWW
ID: 672226

Citar

Texto integral

Acesso aberto
Acesso é fechado

Acesso está concedido
Acesso é fechado

Somente assinantes

Resumo

It was found that the Cp₂ZrCl₂-EtMgBr-catalyzed reaction of 2-alkynylamines with Et₂Zn leads to the regio- and stereoselective formation of (2Z)-allylamines in high yield. It has been established that the presence of morpholyl and piperidyl substituents in the structure of propargylamines does not interfere with the regio- and stereoselective 2-zincoethylzincation of the triple bond. Carbocyclization of α,ω-bis(aminomethyl)alkadiynes based on the Cp₂ZrCl₂-EtMgBr-catalyzed carbozincation reaction with Et₂Zn was carried out for the first time. A mechanism for the catalytic 2-zincoethylzincation of α,ω-bis(aminomethyl)alkadiynes was proposed.

Palavras-chave

2-alkynylamines, 2-zincoethylzincation, α,ω-bis(aminomethyl)alkadiynes, (2Z)-allylamines, zirconocene catalysis, diethylzinc

Texto integral

Bibliografia

Negishi E. Accounts of Chemical Research. 1987, 20, 65–72. doi: 10.1021/ar00134a004
Van Horn D.E., Negishi E. J. Am. Chem. Soc. 1978, 100, 2252–2254. doi: 10.1021/ja00475a058
Negishi E., Kondakov D.Y., Choueiry D., Kasai K., Takahashi T. J. Am. Chem. Soc. 1996, 118, 9577–9588. doi: 10.1021/ja9538039
Normant J.F., Alexakis A. Synthesis. 1981, 1981, 841–870. doi: 10.1055/s-1981-29622.
Halpern J. Angew. Chem., Int. Ed. 1985, 24, 274–282. doi: 10.1002/anie.198502741
Negishi E., Pure Appl. Chem. 1981, 53, 2333–2356. doi: 10.1351/pac198153122333
Negishi E., Van Horn D.E., Yoshida T. J. Am. Chem. Soc. 1985, 107, 6639–6647. doi: 10.1021/ja00309a036
Джемилев У.М., Ибрагимов А.Г., Изв. АН. Сер. хим. 1998, 47, 816–823. [Dzhemilev U.M., Ibragimov A.G. Russ. Chem. Bull. 1998, 47, 786–794.] doi: 10.1007/BF02498144
Джемилев У.М., Ибрагимов А.Г., Рамазанов И.Р., Лукьянова М.П., Шарипова А.З. Изв. АН. Сер. хим. 2001, 50, 465–468. [Dzhemilev U.M., Ibragimov A.G., Ramazanov I.R., Luk’yanova M.P., Sharipova A.Z. Russ. Chem. Bull. 2001, 50, 484–487.] doi: 10.1023/A:1011321526314
Normant J.F., Bourgain M. Tetrahedron Lett. 1971, 12, 2583–2586. doi: 10.1016/S0040-4039(01)96925-4
Shirakawa E., Yamasaki K., Yoshida H., Hiyama T. J. Am. Chem. Soc. 1999, 121, 10221–10222 doi: 10.1021/ja992597s
Suginome M., Shirakura M., Yamamoto A. J. Am. Chem. Soc. 2006, 128, 14438–14439. doi: 10.1021/ja064970j
Daini M., Suginome M. Chem. Commun. 2008, 5224–5226. doi: 10.1039/B809433K
Shirakawa E., Yamagami T., Kimura T., Yamaguchi S., Hayashi T. J. Am. Chem. Soc. 2005, 127, 17164–17165. doi: 10.1021/ja0542136
Fallis A.G., Forgione P. Tetrahedron. 2001, 28, 5899–5913. doi: 10.1016/S0040-4020(01)00422-7
Kadikova R.N., Ramazanov I.R., Mozgovoi O.S., Gabdullin A.M., Dzhemilev U.M. Synlett. 2019, 30, 2019, 311–314. doi: 10.1055/s-0037-1612009
Kadikova R.N., Ramazanov I.R., Gabdullin A.M., Mozgovoi O.S., Dzhemilev U.M. Catalysts. 2019, 9, 1022. doi: 10.3390/catal9121022
Kadikova R.N., Ramazanov I.R., Gabdullin A.M., Mozgovoj O.S., Dzhemilev U.M. RSC Advances. 2020, 10, 17881–17891. doi: 10.1039/D0RA02677H
Kadikova R.N., Ramazanov I.R., Gabdullin A.M., Mozgovoj O.S., Dzhemilev U.M. RSC Advances. 2021, 11, 4631–4638. doi: 10.1039/D0RA10132J
Рамазанов И.Р., Кадикова Р.Н., Джемилев У.М. Изв. АН. Сер. хим.. 2011, 60, 99–106. [Ramazanov I.R., Kadikova R.N., Dzhemilev U.M. Russ. Chem. Bull. 2011, 60, 99–106.] doi: 10.1007/s11172-011-0013-2
Negishi E., Montchamp J.-L., Anastasia L., Elizarov A., Choueiry D. Tetrahedron Lett. 1998, 39, 2503–2506. doi: 10.1016/S0040-4039(98)00349-9
Bieber L.W., Da Silva M.F. Tetrahedron Lett. 2004, 45, 8281–8283. doi: 10.1016/j.tetlet.2004.09.079
Иоффе С.Т., Несмеянов А.Н. Методы элементоорганической химии. Магний, бериллий, кальций, стронций, барий. 1963. М.: Изд-Во Академии Наук СССР, 561 c.