4706-43-8Relevant articles and documents
Atom Transfer Radical Polymerization-Inspired Room Temperature (sp3)C-N Coupling
Coote, Michelle L.,Fung, Alfred. K. K.,Sherburn, Michael S.,Yu, Li-Juan
, p. 9723 - 9732 (2021/07/20)
A simple nonphotochemical procedure is reported for Cu(I)-catalyzed C-N coupling of aliphatic halides with amines and amides. The process is loosely based on the Goldberg reaction but takes place readily at room temperature. It uses Cu(I)Br, a commonly used and inexpensive atom transfer radical polymerization precatalyst, along with the cheap ligand N,N,N′,N″,N″-pentamethyldiethylenetriamine, to activate the R-X bond of the substrate via inner-sphere electron transfer. The procedure brings about productive C-N bond formation between a range of alkyl halide substrates with heterocyclic aromatic amines and amides. The mechanism of the coupling step, which was elucidated through application of computational methods, proceeds via a unique Cu(I) → Cu(II) → Cu(III) → Cu(I) catalytic cycle, involving (a) inner-sphere electron transfer from Cu(I) to the alkyl halide to generate the alkyl radical; (b) successive coordination of the N-nucleophile and the radical to Cu(II); and finally reductive elimination. In the absence of a nucleophile, debrominative homocoupling of the alkyl halide occurs. Control experiments rule out SN-type mechanisms for C-N bond formation.
A convenient way for alkylation of amines using xanthate esters
Sukrutha, Kodipura P.,Swaroop, Toreshettahally R.,Preetham, Ramesh,Lokanath, Neratur K.,Rangappa, Kanchugarakoppal S.,Sadashiva, Maralinganadoddi P.
, p. 2316 - 2323 (2021/06/14)
N-alkylation of amines by the reaction with xanthate esters in the presence of acetic acid catalyst in ethanol is reported. Short reaction time, high yield, general applicability and environmentally benign nature are the noteworthy features of our protocol. The probable mechanism for the formation N-alkylation of amines is proposed.
Synthesis, characterization, and antimicrobial activity of lipophilic N,N′-bis-substituted triazolium salts
Fico, Dominic,Gorden, John D.,Johnson, Shanina S.,King, Lauren B.,Lin, Zi Jie,Martz, Luke,Rodriguez, Isabelle,Shelton, Kerri L.,Ta, Thong,Wilson, Julie A.
supporting information, (2021/11/30)
A series of N,N′-bis-substituted triazolium salts have been synthesized using 1H-1,2,4-triazole, 1H-1,2,3-triazole, and 1H-1,2,3-benzotriazole. Synthesized compounds were tested for their antimicrobial activities against a panel of representative ESKAPE p