ChemInform Abstract: Copper-Catalyzed N-tert-Butylation of Aromatic Amines under Mild Conditions Using tert-Butyl 2,2,2-Trichloroacetimidate (original) (raw)

Copper(II) catalyzed allylic amination of terpenic chlorides in water

Catalysis Communications, 2012

A highly efficient method for the synthesis of allylic amines from terpenic chlorides by cheap copper (II) as catalyst in water has been developed. Allylic chlorides react with high regioselectivity in the presence of secondary amines, under mild conditions to give N-allylic amines in excellent yields.

Copper-catalyzed N-arylation of amines with aryliodonium ylides in water

Beilstein Journal of Organic Chemistry

Copper sulfate catalyzed an efficient, inexpensive, and environment-friendly protocol that has been developed for N-arylation of amines with 1,3-cyclohexadione-derived aryliodonium ylides in water as a green solvent. Aromatic primary amines substituted with electron-donating as well as electron-withdrawing groups on the aryl ring reacted smoothly with iodonium ylides to give the corresponding diarylamines with good to excellent yields. Also, secondary amines underwent N-arylation to deliver tertiary amines with moderate yields.

Copper-Catalyzed Aliphatic C–H Amination with an Amidine Moiety

Organic Letters, 2013

A method for amination of aliphatic CÀH bonds of N-alkylamidines is described that utilizes Cu(OAc) 2 as the catalyst in the presence of PhI(OAc) 2 and K 3 PO 4. The resulting products, dihydroimidazoles and tetrahydropyrimidines, could be converted into the corresponding diamines by hydride reduction.

Copper-catalyzed decarboxylative coupling reactions for the synthesis of propargyl amines

When aryl alkynyl carboxylic acids were allowed to react with amines and aldehydes in CH 3 CN at 80°C in the presence of 10 mol % CuI, the desired propargyl amines were formed in good yields. This coupling reaction demonstrated to work across a broad range of reagents including functionalized aryl alkynyl carboxylic acids, aliphatic and aromatic aldehydes, and cyclic and acyclic amines.

Cu(II)-Mediated Ortho-C–H Amination of Arenes with Free Amines

Journal of Organic Chemistry, 2019

Copper-mediated direct ortho-C-H amination of arenes has been accomplished with the aid of easily removable bidentate pyridine N-oxide as a directing group. The use of free cyclic secondary amines and anilines as aminating agents and inexpensive copper acetate makes the strategy more effective and favorable from the economic point of view. This reaction is compatible with a wide range of functional groups to synthesize a variety of amine-containing products of high interest. This method also allows the short synthesis of central scaffold of pharmaceutically relevant Staphylococcus aureus Sortase A inhibitor.

Catalytic CH Amination with Unactivated Amines through Copper(II) Amides

Angewandte Chemie International Edition, 2010

Alexander von Humboldt Foundation (re-invitation award to T.H.W.), and the Chemical Computing Group (MOE software to T.R.C.). Y.M.B. thanks Georgetown University for a Dissertation Fellowship and M.M.M. is grateful to the Luce Foundation for a predoctoral fellowship.

ChemInform Abstract: Copper-Catalyzed Coupling of Aryl Chlorides, Bromides and Iodides with Amines and Amides

ChemInform, 2009

A copper(I) catalyzed procedure for carbon-nitrogen bond formation utilizing aryl halides and either amines, including amino acids and diphenylamine, or aliphatic and aromatic amides is described. a Reaction conditions: aryl halide (2.0 mmol), Cu 2 O (5 mol%), amine (4.0 mmol) in NMP, 80 1C, 24 h. b Isolated yields. c NaOtBu (4.0 mmol), 100 1C. d 110 1C. e NaOtBu (3.0 mmol), 90 1C.

Copper-Mediated Amination of Aryl C-H Bonds with the Direct Use of Aqueous Ammonia via a Disproportionation Pathway

Journal of the American Chemical Society, 2018

The direct amination of C-H bonds with ammonia is a challenge in synthetic chemistry. Herein, we present a copper-mediated approach that enables a chelation-assisted aromatic C-H bond amination using aqueous ammonia. A key strategy was to use soft low-valent Cu(I) species to avoid the strong coordination of ammonia. Mechanistic investigations suggest that the catalysis is initiated by a facile deprotonation of bound ammonia, and the C-N coupling is achieved by subsequent reductive elimination of the resultant copper-amido intermediate from a Cu(III) intermediate that is readily generated by disproportionation of low-valent copper analogues. This mechanistic postulate was supported by a preliminary kinetic isotope effect study and computations. This new chelation-assisted, copper-mediated C-H bond amination with aqueous ammonia was successfully applied to a broad range of substrates to deliver primary anilines. Moreover, the mild conditions required for this transformation allowed th...