2998-92-7

Upstream product

• 64-17-5 ethanol 
• 2998-91-6 p-tolyl phenyl ketoxime 
• 134-84-9 4-Methylbenzophenone 
• 110-86-1 pyridine 
• 5720-05-8 4-methylphenylboronic acid 
• 698-16-8 benzohydroximoyl chloride 
• 100-52-7 benzaldehyde 
• 932-90-1 Benzaldoxime 

Downstream Products

• 6833-18-7 4-methyl-N-phenylbenzamide 
• 582-78-5 N-(4-methylphenyl)benzamide 
• 42449-48-9 (Z)-α-(4-Methylphenyl)-α-phenyl-N-methylnitrone 
• 42449-49-0 (Z)-4-methylbenzophenone O-methyl oxime 
• 40463-60-3 anti-4-Methylbenzophenon-oxim-chloroformat 
• 59484-05-8 Z-p-Methyl-benzophenon-oxim-phenyl-carbonat 
• 59484-14-9 4-Methyl-N-phenyl-benzimidic acid phenyl ester 

Relevant academic research and scientific papers

Transition-Metal-Free Coupling of 1,3-Dipoles and Boronic Acids as a Sustainable Approach to C?C Bond Formation

The need for alternative, complementary approaches to enable C?C bond formation within organic chemistry is an on-going challenge in the area. Of particular relevance are transformations that proceed in the absence of transition-metal reagents. In the current study, we report a comprehensive investigation of the coupling of nitrile imines and aryl boronic acids as an approach towards sustainable C?C bond formation. In situ generation of the highly reactive 1,3-dipole facilitates a Petasis–Mannich-type coupling via a nucleophilic boronate complex. The introduction of hydrazonyl chlorides as a complementary nitrile imine source to the 2,5-tetrazoles previously reported by our laboratory further broadens the scope of the approach. Additionally, we exemplify for the first time the extension of this protocol into another 1,3-dipole, through the synthesis of aryl ketone oximes from aryl boronic acids and nitrile N-oxides.

Stereospecific 1,4-Metallate Shift Enables Stereoconvergent Synthesis of Ketoximes

Reported herein is a stereospecific 1,4-metallate rearrangement for single-geometry ketoxime synthesis from oxime chlorides and arylboronic acids. This strategy exhibits broad substrate scope with excellent stereoselectivity under mild reaction conditions. In comparison with the conventional approaches, each configuration of unsymmetric diaryl oximes, as well as the thermodynamically less stable Z isomer of aryl alkyl ketoximes can be selectively and exclusively obtained. The reactivities of unsymmetric diaryl oximes and the Z isomer of aryl alkyl oximes, a class of underexplored molecules, enables efficient access to the corresponding isoquinolines, isoquinoline N-oxides, and amides having a single configuration.