135664-52-7

Upstream product

• 5422-88-8 phenyl cyclopentyl ketone 
• 6740-66-5 (1-bromocyclopentyl)(phenyl)methanone 
• 55305-43-6 N-cyano-N-phenyl-p-toluenesulfonamide 
• 29739-46-6 1,1-cyclopentanedicarbonitrile 
• 98-80-6 phenylboronic acid 
• 100-58-3 phenylmagnesium bromide 
• 24214-78-6 N'-cyclopentylidene benzohydrazide 
• 143-33-9 sodium cyanide 

Relevant academic research and scientific papers

Access to α-Cyano Carbonyls Bearing a Quaternary Carbon Center by Reductive Cyanation

Reductive cyanation of tertiary alkyl bromides using electrophilic cyanating reagent and zinc reductant was developed, providing various α-cyano ketones, esters, and carboxamides containing a nitrile-bearing all-carbon quaternary center in good to excellent yields under mild reaction conditions. The corresponding reaction mechanism involving in situ generated organozinc reagent and reactivity distinction was elucidated by density functional theory computation.

Rhodium-Catalyzed Addition of Aryl Boronic Acids to 2,2-Disubstituted Malononitriles

β-Ketonitriles bearing a quaternary carbon at the 2-position were prepared through Rh-catalyzed addition of aryl boronic acids to 2,2-disubstituted malononitriles. In contrast to the previously described transnitrilative cyanation of aryl boronic acids with dialkylmalononitriles, the present reaction avoids retro-Thorpe collapse of the intermediate addition product through the use of a milder base. The reaction was amenable to a variety of aryl boronic acids and disubstituted malononitriles, providing a diverse array of β-ketonitriles. The products could be further derivatized to valuable chiral α,α-disubstituted-β-aminonitriles through addition reactions to the corresponding N-tert-butanesulfinyl imines.

Study of the chemoselectivity of Grignard reagent addition to substrates containing both nitrile and Weinreb amide functionalities

Several substrates containing both cyano and Weinreb amide functionalities have been synthesized to study the chemoselectivity of their reactions with organomagnesium bromides (ArMgBr and RMgBr). Excellent chemoselectivity towards the Weinreb amide was observed in most cases, even in the presence of excess Grignard reagent, affording cyano ketones in good-to-excellent yields. The reactions of various substrates containing both nitrile and Weinreb amide functionalities with Grignard reagents have been studied. The Weinreb amide reacts chemoselectively with excess Grignard reagent to give the corresponding cyano ketones in good yields. This chemoselectivity has been exploited for the synthesis of a key coumarin intermediate towards the 5-lipoxygenase inhibitor MK-0633. Copyright

Phase-Transfer Catalyzed Formation of α-Cyano Ketones from Ketone Aroylhydrazones in NaCN(aq)-Inert Organic Solvent System

α-Cyanoalkyl aryl ketones can be obtained from ketone aroylhydrazones by heterogeneous reaction with aqueous sodium cyanide, an inert organic solvent, and acetic acid in the presence of air and a catalytic amount of a quaternary ammonium salt.The initiall