950851-02-2Relevant academic research and scientific papers
Lewis acid mediated vinyl-transfer reaction of alkynes to N-alkylimines by using the N-alkyl residue as a sacrificial hydrogen donor
Malakar, Chandi C.,Stas, Sara,Herrebout, Wouter,Tehrani, Kourosch Abbaspour
supporting information, p. 14263 - 14270 (2017/07/18)
A variety of N-alkyl-α,α-dichloroaldimines were vinylated by terminal acetylenes in the presence of Lewis acids such as In(OTf)3 or BF3 ?OEt2 and hexafluoroisopropanol (HFIP) as an additive. The reaction proceeds at ambient temperature and leads to geometrically pure allylic β,β-dichloroamines. This approach is complementary to previously reported transition-metal-catalyzed vinyl-transfer methods, which are not applicable to aliphatic imines and are restricted to imines that contain an electron-withdrawing nitrogen substituent. In the present approach, terminal alkynes were used as a source of the vinyl residue, and the N-alkyl moiety of the imine acts as a sacrificial hydrogen donor. The additional advantage of this methodology is the fact that no external toxic or hazardous reducing agents or molecular hydrogen has to be used. This new methodology nicely combines a C(sp2))-C(sp) bond formation, hydride transfer, and an unusual cleavage of an unactivated C-N bond, thereby giving rise to functionalized primary allylic amines. A detailed experimental study supported by DFT calculations of the mechanism has been done.
An indium(III)-catalyzed synthesis of 4,4-dichloro-1-aryl-N-alkyl-1-yn-3- amines via an intermolecular C(sp2)-C(sp) bond formation
Malakar, Chandi C.,Maes, Bert U. W.,Tehrani, Kourosch Abbaspour
supporting information, p. 3461 - 3467 (2013/02/22)
This paper demonstrates an indium(III) triflate-catalyzed reaction of electron-deficient α,α-dichloroaldimines with terminal alkynes leading to a rapid and selective access to highly functionalized propargylic amines in good to excellent yields. The dichloromethylene moiety of the aldimine acts as an activating group to accomplish this transformation under very mild conditions.
Lewis acid promoted Mannich type reactions of α,α-dichloro aldimines with potassium organotrifluoroborates
Stas, Sara,Tehrani, Kourosch Abbaspour
, p. 8921 - 8931 (2008/02/10)
Potassium phenylethynyltrifluoroborate and potassium styryltrifluoroborates react with α,α-dichlorinated aldimines in the presence of BF3·OEt2 as a Lewis acid to give a new stable class of functionalized propargylamines and allylamin
