7694-50-0Relevant academic research and scientific papers
Reactions of sulfur- and phosphorus-substituted fluoroalkylating silicon reagents with imines and enamines under acidic conditions
Kosobokov, Mikhail D.,Dilman, Alexander D.,Struchkova, Marina I.,Belyakov, Pavel A.,Hu, Jinbo
supporting information; experimental part, p. 2080 - 2086 (2012/04/23)
Nucleophilic fluoroalkylation reactions of imines and enamines with α-phenylthio, α-phenylsulfonyl, and α-diethylphosphoryl substituted fluorinated silanes have been investigated. The reactions are promoted by hydrofluoric acid generated in situ from pota
(t-Bu)2PN=P(i-BuNCH2CH2)3N: New efficient ligand for palladium-catalyzed C-N couplings of aryl and heteroaryl bromides and chlorides and for vinyl bromides at room temperature
Reddy, Ch. Venkat,Kingston, Jesudoss V.,Verkade, John G.
, p. 3047 - 3062 (2008/09/19)
(Chemical Equation Presented) By employing Pd(OAc)2, Cs 2CO3, or NaOH, and the new ligand (t-Bu) 2PN=P(i-BuNCH2CH2)3N (3a), an electronically diverse array of aryl bromides and chlorides possessing base-sensitive substituents (nitro, ester, and keto) provide coupling products with bulky aryl amines in good to excellent yields. Aryl halides possessing other functional groups including cyano, amino, trifluoromethyl, and phenol, coupled with equal ease, producing highly functionalized amines in good to excellent yields. Moreover, an aryl chloro group can be preserved in the presence of a bromo substituent under our reaction conditions. BOC-protected amines also participated efficiently. Heterocyclic bromides and chlorides underwent clean couplings with amines in excellent yields. An important strength of our protocol is the use of lower palladium loadings than those reported earlier, without compromising yields. The air-stable palladium complex (η3-cinnamyl)PdCl·(3a) (5) was also employed successfully in C-N coupling reactions while the crotyl analogue was less efficacious. The 3a/Pd(OAc)2 catalyst system promotes, for the first time, efficient coupling of vinyl bromides with a variety of amines to produce imines and enamines at room temperature.
Preparation of tertiary alkyl carbinamines, propargylamines, and α-heteroarylamines by ketone-based aminoalkylation
Katritzky, Alan R.,Yang, Hongfang,Singh, Sandeep K.
, p. 286 - 290 (2007/10/03)
(Chemical Equation Presented). Ketones 6a-i were converted into their benzotriazolylamine adducts 8a-i either directly from the corresponding ketone 6a or via enamines 7b-i. Adducts 8a-i on treatment with Grignard reagents, lithium phenylacetylide, or heteroaryllithiums gave tertiary alkyl carbinamines 9a-h (47-61%), propargylamines 10a-i (30-98%), and α-heteroarylamines 11a-k (44-85%), respectively.
Novel method for the synthesis of enamines by palladium catalyzed amination of alkenyl bromides
Barluenga, Jose,Fernandez, M. Alejandro,Aznar, Fernando,Valdes, Carlos
, p. 2362 - 2363 (2007/10/03)
The intermolecular palladium catalyzed cross-coupling reaction between secondary amines and alkenyl bromides is described for the first time, giving rise to enamines with very high yields and regioselectivity.
Optimum Conditions for Enamine Synthesis by an Improved Titanium Tetrachloride Procedure
Carlson, Rolf,Nilsson, Asa,Stroemqvist, Mats
, p. 7 - 14 (2007/10/02)
A modified procedure for enamine synthesis which results in shorter times and increased yield has been developed.Optimum conditions for the synthesis have been obtained from a series of eight different acyclic ketones with three different amines.The optimum conditions were determined either by response surface methodologgy or by simplex technique.In view of the results some consideration of the mechanism is briefly discussed.
