405518-83-4Relevant academic research and scientific papers
Direct electrophilic diamination of functionalized alkenes without the use of any metal catalysts
Chen, Dianjun,Timmons, Cody,Wei, Han-Xun,Li, Guigen
, p. 5742 - 5745 (2003)
A new direct electrophilic diamination reaction of α,β-unsaturated ketones and esters has been established without the use of any metal catalysts. Three types of nitriles (CH3CN, CH3CH2CN, and CH3CH2CH2CN) were employed as nucleophilic nitrogen sources. A new mechanism has also been proposed to explain the resulting regio- and stereoselectivity.
A novel electrophilic diamination reaction of alkenes
Li, Guigen,Wei, Han-Xun,Kim, Sun Hee,Carducci, Michael D.
, p. 4277 - 4280 (2001)
A three-component electrophilic reaction transforms olefins into imidazoline and diamine derivatives (see scheme). Rhodium(II) heptafluorobutyrate dimer (2 mol%) was utilized as the catalyst and N,N-dichloro-p-toluenesulfonamide (TsNCl2) and ac
Electrophilic diamination of alkenes by using FeCl(3)-PPh(3) complex as the catalyst.
Wei, Han-Xun,Kim, Sun Hee,Li, Guigen
, p. 4777 - 4781 (2002)
The FeCl(3)-PPh(3) complex was found to effectively catalyze the electrophilic diamination reaction of electron-deficient alkenes. Improvements on yields and stereoselectivity have been achieved for both alpha,beta-unsaturated carboxylic esters and ketones. Under the new catalytic system, alpha,beta-unsaturated carboxylic esters were found to be superior to their ketone counterparts, which is opposite to the previous (C(3)F(7)CO(2))(2)Rh](2)-catalyzed diamination. The reaction employs readily available N,N-dichloro-p-toluenesulfonamide (TsNCl(2)) and acetonitrile as the nitrogen sources and is very easy to perform at room temperature without the special protection of inert gases. The resulting diamino products belong to imidazolidine analogue and can further strengthen the importance of the new reaction. Modest to good yields (52-84%) and high regio- and stereoselectivity have been achieved for 10 examples.
The combination of TsNH2 and NCS as nitrogen and chlorine sources for direct diamination of enones
Timmons, Cody,Chen, Dianjun,Xu, Xin,Li, Guigen
, p. 3850 - 3854 (2003)
The regio-, stereo-, and chemoselective diamination of enones has been achieved without the observation of any haloamines. The reaction employs the readily available inexpensive combination of NCS and TsNH2 as an electrophilic nitrogen source, and three nitriles as nucleophilic nitrogen sources. A novel mechanism involving the formation of aziridinium intermediates from the reaction of TsNHCl with olefins and a new [2+3] cyclic addition for aziridinim ring opening has been proposed for the electrophilic diamination of olefins. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
Organocatalyzed regio- and stereoselective diamination of functionalized alkenes
Wu, Hui,Ji, Xiaoyun,Sun, Hao,An, Guanghui,Han, Jianlin,Li, Guigen,Pan, Yi
, p. 4555 - 4559 (2010)
The first organocatalyzed diamination reaction of alkenes with N,N-dichlorotoluenesulfonamide (TsNCl2) and acetonitrile as nitrogen sources was reported. The catalytic diamination reaction was convenient to carry out, resulting in imidazoline products with good yields and excellent regio- and stereoselectivities. Several other organic molecules were also tried as catalyst for this reaction and good results were achieved. A new one-pot synthesis of vicinal diamines via the current PPh3-catalyzed diamination and the hydrolysis of resulting imidazoline products with SnCl4 as promoter was also established.
