1375414-72-4Relevant academic research and scientific papers
Synthesis method of 2, 2-dimethyl-4-phenylpent-4-enitrile compound
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Paragraph 0039-0057, (2020/08/25)
The invention discloses a synthesis method of a 2, 2-dimethyl-4-phenylpentyl-4-enitrile compound. The synthesis method comprises the following step: carrying out one-pot reaction on an alpha-methyl-aryl ethylene compound and AIBN under the catalysis of elemental iodine to obtain the 2, 2-dimethyl-4-phenylpentyl-4-enitrile compound. The method does not need to adopt a metal catalyst and a toxic solvent and is beneficial to environmental protection, mild in reaction condition, simple in step, high in target product yield, high in atom utilization rate and beneficial to industrial production.
Metal-Free-Catalyzed Synthesis of Allyl Nitriles via Csp2-Csp3 Coupling between Olefins and Azobis (Alkyl-carbonitrile)
Cao, Zhong-Zhong,Nie, Zhiwen,Yang, Tonglin,Su, Miaodong,Li, Hui,Luo, Wei-Ping,Liu, Qiang,Guo, Can-Cheng
, p. 3287 - 3296 (2020/03/23)
The metal-free-catalyzed synthesis of allyl nitriles from Csp2-Csp3 coupling between olefins and azobis was carried out. Key on this work was that the synthesis of allyl nitriles directly using olefin as a start
Catalytic Asymmetric Radical Diamination of Alkenes
Wang, Fu-Li,Dong, Xiao-Yang,Lin, Jin-Shun,Zeng, Yang,Jiao, Guan-Yuan,Gu, Qiang-Shuai,Guo, Xian-Qi,Ma, Can-Liang,Liu, Xin-Yuan
supporting information, p. 979 - 990 (2017/12/26)
Catalytic asymmetric diamination of alkenes is a highly attractive method for creating chiral vicinal diamines, which are ubiquitous in biologically active molecules and versatile ligands as well as organocatalysts. We report the use of O-acylhydroxylamines as dialkylaminyl radical precursors to trigger asymmetric diamination of alkene under Cu(I)/chiral phosphoric acid dual catalysis. This reaction allows for direct alkylamine incorporation and features high enantioselectivity, a broad substrate scope, wide functional-group tolerance, and mild reaction conditions, providing convenient and practical access to a wide range of highly enantio-enriched β-alkylamine-containing pyrrolidines. We have also achieved asymmetric azidoamination of alkenes by using azidoiodinane as an azidyl radical precursor, offering a complementary method for preparing diverse chiral β-amino pyrrolidines. The application of the resultant α-tertiary pyrrolidine-derived diamine was showcased to significantly promote the enantioselectivity of an asymmetric Michael reaction. Chiral vicinal diamines are characteristic and essential motifs embedded in numerous biologically active molecules. In addition, they are also the core scaffolds for a diverse range of chiral ligands, organocatalysts, and auxiliaries widely used in organic synthesis. For their preparation, asymmetric diamination of readily available alkenes constitutes an expedient and important method for accessing enantio-enriched vicinal diamines. However, none of the known strategies are able to directly introduce a protection-free alkyl amine moiety, mainly because of its strong coordination capability, mostly leading to transition-metal catalyst poisoning and susceptibility to oxidation. As a consequence, both the step economy and amine scope are compromised, thus limiting broad applicability. Here, we report the asymmetric radical diamination of alkenes under Cu(I)/chiral phosphoric acid dual catalysis, enabling direct incorporation of alkyl amine groups. Liu and colleagues describe the asymmetric radical diamination of alkenes triggered by intermolecular addition of dialkylaminyl or azidyl radical to the alkene under Cu(I)/chiral phosphoric acid dual catalysis. This reaction enables direct incorporation of alkylamine moieties and provides convenient and practical access to a wide range of highly enantio-enriched β-alkylamine-containing pyrrolidines. Moreover, the resulting α-tertiary pyrrolidine-derived diamine proves to significantly promote the enantioselectivity of an asymmetric Michael reaction.
