107743-99-7Relevant academic research and scientific papers
Preparation of cyclic imides from alkene-tethered amides: Application of homogeneous Cu(ii) catalytic systems
Chen, Suqing,Liu, Zhenghui,Mu, Tiancheng,Ou, Hualin,Tan, Xingxing,Wang, Peng,Yan, Zhenzhong,Yu, Dongkun,Zhao, Xinhui
, p. 7698 - 7707 (2020)
A Cu-based homogeneous catalytic system was proposed for the preparation of imides from alkene-tethered amides. Here, O2 acted as a terminal oxidant and a cheap and easily available oxygen source. The cleavage of CC bonds and the formation of C
Iodoarene-Catalyzed Oxyamination of Unactivated Alkenes to Synthesize 5-Imino-2-Tetrahydrofuranyl Methanamine Derivatives
Deng, Xiao-Jun,Liu, Hui-Xia,Zhang, Lu-Wen,Zhang, Guan-Yu,Yu, Zhi-Xiang,He, Wei
, p. 235 - 253 (2021/01/09)
Reported here is the room-temperature metal-free iodoarene-catalyzed oxyamination of unactivated alkenes. In this process, the alkenes are difunctionalized by the oxygen atom of the amide group and the nitrogen in an exogenous HNTs2 molecule. This mild and open-air reaction provided an efficient synthesis to N-bistosyl-substituted 5-imino-2-tetrahydrofuranyl methanamine derivatives, which are important motifs in drug development and biological studies. Mechanistic study based on experiments and density functional theory calculations showed that this transformation proceeds via activation of the substrate alkene by an in situ generated cationic iodonium(III) intermediate, which is subsequently attacked by an oxygen atom (instead of nitrogen) of amides to form a five-membered ring intermediate. Finally, this intermediate undergoes an SN2 reaction by NTs2 as the nucleophile to give the oxygen and nitrogen difunctionalized 5-imino-2-tetrahydrofuranyl methanamine product. An asymmetric variant of the present alkene oxyamination using chiral iodoarenes as catalysts also gave promising results for some of the substrates.
Deoxygenative α-alkylation and α-arylation of 1,2-dicarbonyls
Arman, Hadi D.,Dang, Hang T.,Haug, Graham C.,Jin, Shengfei,Larionov, Oleg V.,Nguyen, Viet D.
, p. 9101 - 9108 (2020/09/17)
Construction of C-C bonds at the α-carbon is a challenging but synthetically indispensable approach to α-branched carbonyl motifs that are widely represented among drugs, natural products, and synthetic intermediates. Here, we describe a simple approach to generation of boron enolates in the absence of strong bases that allows for introduction of both α-alkyl and α-aryl groups in a reaction of readily accessible 1,2-dicarbonyls and organoboranes. Obviation of unselective, strongly basic and nucleophilic reagents permits carrying out the reaction in the presence of electrophiles that intercept the intermediate boron enolates, resulting in two new α-C-C bonds in a tricomponent process. This journal is
Effects of α-Substitution on the Rate of Chloromercuriolactonization of Phenyl Esters of γδ-Unsaturated Acids
de Almeida, Maria I.,do Amaral, Antonia T.,do Amaral, Luciano
, p. 1953 - 1958 (2007/10/02)
Second-order rate constants for the reaction of several phenyl esters of α-alkyl- and/or α-aryl-substituted allyacetic acids with mercury(II) chloride have been determined in 50percent aqueous ethanol.It was found that α-substitution increases the rate of reaction.The rate constants can be correlated with the dual substituent parameter expressions (i) and (ii).In the systems studied the steric coefficient is much larger than the polar one, suggesting that the effect of the substituents on the rate of the reaction is essentially steric in nature, with a small additional contribution from the polar effect. log k2 = log k2o + ρ*?* + δEs (i). log k2 = log k2o + ρ*?* + ψν (ii)
