Nickel-Catalyzed β-Carboxylation of Ynamides with Carbon Dioxide

Nickel-Catalyzed β-Carboxylation of Ynamides with Carbon Dioxide
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镍催化二氧化碳与酰胺的 β-羧化反应

DOI:
10.1055/s-0037-1611529
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发表时间:
2019
期刊:
影响因子:
2
通讯作者:
Sato Yoshihiro
Sato Yoshihiro
中科院分区:
化学4区
文献类型:
--
作者:
Doi Ryohei;Okano Taichi;Abdullah Iman;Sato Yoshihiro

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本文报道了镍催化的β-选择性氢化羰基化反应合成保护的β-氨基酸。排他性β-选择性的关键是在镁盐存在下使用二乙基锌作为还原剂。该反应用双(乙酰丙酮)合镍(II)代替昂贵且敏感的双(1,5-环辛烷)合镍(0)进行。此外,优化的配体是廉价的1,5-环辛二烯。底物范围的研究表明,氮和炔的取代基对反应效率有显着的影响。我们获得的实验线索表明,形成的乙烯基锌中间体,形成C-C键与CO2。
A nickel-catalyzed β-selective hydrocarboxylation of ynamides to give protected dehydro-β-amino acids was developed. The key to exclusive β-selectivity was the use of diethylzinc as a reductant in the presence of a magnesium salt. The reaction was conducted with bis(acetylacetonato)nickel(II) instead of costly and sensitive bis(1,5-cyclooctadiene)nickel(0). In addition, the optimized ligand was inexpensive 1,5-cyclooctadiene. Investigation of the substrate scope revealed that both nitrogen and alkyne substituents have marked effects on the reaction efficiency. We obtained experimental clues that indicated the formation of a vinylzinc intermediate that forms a C–C bond with CO2.
DOI: 10.1021/ol801534e
发表时间: 2008-09-04
期刊: ORGANIC LETTERS
影响因子: 5.2
作者:
Saito, Nozomi;Katayama, Tomoyuki;Sato, Yoshihiro
通讯作者: Sato, Yoshihiro
有机锌试剂和二氧化碳铜催化的酰胺烷基化羧化反应
DOI: --
发表时间: 2013
期刊:
影响因子: --
作者:
Takimoto Masanori;Hou Zhaomin
通讯作者: Hou Zhaomin