16141-50-7

Upstream product

• 536-74-3 phenylacetylene 
• 201024-81-9 C,N-diphenylnitrone 
• 1137-96-8 N-(benzylidene)aniline N-oxide 
• 538-51-2 benzylidene phenylamine 
• 103-80-0 phenylacetyl chloride 
• 201230-82-2 carbon monoxide 
• 100-44-7 benzyl chloride 
• 103-82-2 phenylacetic acid 
• 62-53-3 aniline 
• 100-52-7 benzaldehyde 
• 3282-32-4 2-diazo-acetophenone 

Downstream Products

• 538-51-2 benzylidene phenylamine 
• 103-30-0 (E)-1,2-diphenyl-ethene 
• 54746-64-4 N,2,3-triphenylacrylamide 
• 3210-15-9 N-phenyl-2,3-diphenylpropanamide 
• 73308-42-6 N-benzyl-N-phenyl-2-phenylacetamide 

Relevant academic research and scientific papers

CuFe2O4nanoparticles catalyze the reaction of alkynes and nitrones for the synthesis of 2-azetidinones

CuFe2O4 nanoparticles acted as a highly efficient heterogeneous catalyst in the reaction of alkynes and nitrones (Kinugasa reaction) for the synthesis of various 2-azetidinones. In all cases, the reactions proceeded conveniently under mild conditions with good-to-excellent yields and with a wide range of functional-group tolerance. The catalyst could be separated readily using an external magnet. This journal is

Synthesis of Exclusively 4-Substituted β-Lactams through the Kinugasa Reaction Utilizing Calcium Carbide

A new Kinugasa reaction protocol has been elaborated for the one-pot synthesis of 4-substituted β-lactams utilizing calcium carbide and nitrone derivatives. Calcium carbide is thereby activated by TBAF·3H2O in the presence of CuCl/NMI. The ease of synthesis and use of inexpensive chemicals provides rapid access of practical quantities of β-lactams exclusively substituted at position 4.

A Revised Mechanism for the Kinugasa Reaction

Detailed kinetic analysis for the Cu(I)-catalyzed Kinugasa reaction forming β-lactams has revealed an anomalous overall zero-order reaction profile, due to opposing positive and negative orders in nitrone and alkyne, respectively. Furthermore, the reaction displays a second-order dependence on the catalyst, confirming the critical involvement of a postulated bis-Cu complex. Finally, reaction progress analysis of multiple byproducts has allowed a new mechanism, involving a common ketene intermediate to be delineated. Our results demonstrate that β-lactam synthesis through the Kinugasa reaction proceeds via a cascade involving (3 + 2) cycloaddition, (3 + 2) cycloreversion, and finally (2 + 2) cycloaddition. Our new mechanistic understanding has resulted in optimized reaction conditions to dramatically improve the yield of the target β-lactams and provides the first consistent mechanistic model to account for the formation of all common byproducts of the Kinugasa reaction.

One-pot synthesis of trans-β-lactams from ferrocenylketene generated by thermal Wolff rearrangement

A series of β-lactams containing the ferrocene moiety were synthesized through the Staudinger reaction between ferrocenylketene generated by the thermal Wolff rearrangement of the corresponding diazo ketone and various imines. The stereochemical outcome h

Carbocation catalyzed carboxylic acid activation in Staudinger reaction for stereoselective synthesis of β-lactams

A novel strategy to synthesize stereoselective β-lactams has been disclosed via cyclopropenium-ion-catalyzed reaction of substituted acetic acids with aldimines under mild conditions. Products are formed in high yields (86–95%) and good diastereoselectivi

Asymmetric synthesis of trans-β-lactams by a Kinugasa reaction on water

The asymmetric Kinugasa reaction was performed on pure water for the first time without the need for any organic co-solvents. In contrast to most asymmetric Kinugasa reactions, trans-β-lactams were obtained as the major products in good yields, enantioselectivities, and diastereoselectivities (up to 90 % yield, 98 % ee, and >99:1 d.r.). This reaction is atom-economical, environmentally friendly, and affords synthetically useful but challenging products. Walking on water: Asymmetric Kinugasa reactions on pure water without any organic co-solvents afforded synthetically useful trans-β-lactams in good yields, enantioselectivities, and diastereoselectivities (up to 90 % yield, 98 % ee, and >99:1 d.r.). Copyright

Studies of multicomponent Kinugasa reactions in aqueous media

Micelle-promoted, copper-catalyzed multicomponent Kinugasa reactions were studied in aqueous media. Reactions were performed in a 'single pot' for a series of in situ generated C,N-diphenylnitrones with Cu(I) phenylacetylide providing β-lactams in yields of 45-85%. Substituents affect the reaction by either accelerating cycloaddition or minimizing side reactions.

Stereoselective synthesis of 3,4-diaryl β-lactams

Novel 3,4-diaryl β-lactams were prepared with high stereoselectivity in an efficient manner by a palladium-catalyzed [2+2] carbonylative cycloaddition of benzyl halides with heteroarylidene amines. The type of alkyl group linked to the nitrogen atom influences the reaction's stereoselectivity. Moreover, using chiral imines, separable diastereomeric mixtures of chiral 3,4-diaryl-β-lactams were isolated with good yields and high trans diastereoselections.

Cycloreversion of azetidines via oxidative electron transfer. Steady-state and time-resolved studies

(Chemical Equation Presented) Cycloreversion of cis- and trans-1,2,3-triphenylazetidine (c-2 and t-2) is achieved by electron transfer to (tris(4-bromophenyl)aminium radical cation (5?+). Stepwise C-N and C-C bond cleavage of azetidine radical cations leads to cis- and trans-stilbene, together with N-benzylideneaniline, as final products. Mechanistic evidence is provided by quenching studies, using laser flash photolysis to generate 5?+ from its neutral precursor.

Trisoxazoline/Cu(II)-promoted Kinugasa reaction. Enantioselective synthesis of β-lactams

The reactions of nitrones with terminal alkynes, catalyzed by chiral iPr-trisoxazoline 23/Cu(ClO4)2·6H 2O under air atmosphere, afforded β-lactams in moderate to good yields with up to 85% ee. The diastereoselec