2909-32-2

Upstream product

• 98-98-6 2-Picolinic acid 
• 618-36-0 rac-methylbenzylamine 
• 100-70-9 2-Cyanopyridine 
• 98-85-1 1-Phenylethanol 
• 50919-07-8 1-(3-methoxy-phenyl)-ethylamine 
• 541-41-3 chloroformic acid ethyl ester 
• 69157-32-0 picolinic acid 
• 492-73-9 2,2'-Pyridil 
• 39901-94-5 2-picolinoyl chloride hydrochloride 
• 100-46-9 benzylamine 
• 18904-38-6 N-benzyl-2-pyridinecarboxamide 

Downstream Products

• 22875-84-9 2,3-diphenyl-1-butene 
• 1404616-90-5 N-(1-(3-methoxy-6-(n-butylthio)phenyl)-1-methylethyl)picolinamide 
• 1404616-91-6 N-(1-(3-methoxy-2,6-di(n-butylthio)phenyl)-1-methylethyl)picolinamide 
• 93472-50-5 1-methyl-3,4-diphenylisoquinoline 
• 1721-96-6 1-methyl-3-phenylisoquinoline 

Relevant academic research and scientific papers

Tropylium-promoted Ritter reactions

The Ritter reaction used to be one of the most powerful synthetic tools to functionalize alcohols and nitriles, providing valuableN-alkyl amide products. However, this reaction has not been frequently used in modern organic synthesis due to its employment of strongly acidic and harsh reaction conditions, which often lead to complicated side reactions. Herein, we report the development of a new method using salts of the tropylium ion to promote the Ritter reaction. This method works well on a range of alcohol and nitrile substrates, giving the corresponding products in good to excellent yields. This reaction protocol is amenable to microwave and continuous flow reactors, offering an attractive opportunity for further applications in organic synthesis.

Cobalt-Mediated Decarboxylative/Desilylative C?H Activation/Annulation Reaction: An Efficient Approach to Natural Alkaloids and New Structural Analogues

A Co(II)-mediated decarboxylative/desilylative C?H activation/annulation reaction for the efficient synthesis of 3-arylisoquinolines has been developed. Using alkynyl carboxylic acid and alkynyl silane as terminal alkyne precursors, providing straightforw

Cobalt-Catalyzed, Directed C-H Functionalization/Annulation of Phenylglycinol Derivatives with Alkynes

A new method for cobalt-catalyzed C(sp2)-H functionalization of phenylglycinol derivatives with terminal and internal alkynes directed by picolinamide auxiliary has been developed. This method offers an efficient and highly regioselective route for the synthesis of 1-hydroxymethyltetrahydroisoquinolines. The reaction employs commercially available Co(II) catalyst in the presence of Mn(III) cooxidant and oxygen as a terminal oxidant and proceeds with full preservation of original stereochemistry.

Oxidative C-H/N-H Annulation of Aromatic Amides with Dialkyl Malonates: Access to Isoindolinones and Dihydrobenzoindoles

A copper-mediated oxidative C-H/N-H annulation of aromatic amides with dialkyl malonates has been presented to afford synthetically valuable dihydrobenzoindoles and isoindolinones. The reaction proceeds through direct oxidative C(sp2)-H/C(sp3)-H coupling followed by an intramolecular N-H/C(sp3)-H dehydrogenative coupling to deliver the target motifs with broad scope and functional group tolerance.

Highly chemoselective, sterically sensitive NHC-catalysed amine acylation with pyridil

A new strategy for the protection of amines has been developed involving reaction with pyridil under the influence of N-heterocyclic carbene catalysis. The methodology is capable of distinguishing between two amines characterised by small differences in steric bulk and the resulting pyridoyl amides can be cleaved without requiring either strongly acidic or basic hydrolysis.

Cobalt-Catalyzed ortho-C?H Functionalization/Alkyne Annulation of Benzylamine Derivatives: Access to Dihydroisoquinolines

A practical picolinamide-directed C?H functionalization/alkyne annulation of benzylamine derivatives enabling access to the previously elusive 1,4-dihydroisoquinoline skeleton was developed using molecular O2 as the sole oxidant and Co(OAc)2 as precatalyst. The method is compatible with both internal and terminal alkynes and shows high versatility and functional-group tolerance. Furthermore, full preservation of enantiopurity is observed when using non-racemic α-substituted benzylamine derivatives. Kinetic analysis of the reagents and catalyst, labeling experiments, and the isolation and identification of catalytically competent Co-complexes revealed important insights about the mechanism.

Cobalt-Catalyzed Selective Synthesis of Isoquinolines Using Picolinamide as a Traceless Directing Group

Picolinamide has first been employed as a traceless directing group for the cobalt-catalyzed oxidative annulation of benzylamides with alkynes to synthesize isoquinolines through C-H/N-H bonds activation. Oxygen is used as a terminal oxidant. This protocol exhibits good functional group tolerance and excellent regioselectivity. Both terminal and internal alkynes can be efficiently applied to this catalytic system as substrates.

Co(II)-Catalyzed Regioselective Cross-Dehydrogenative Coupling of Aryl C-H Bonds with Carboxylic Acids

A cobalt(II)-catalyzed regioselective aryl C-H bond oxygenation between arenes and aryl or aliphatic carboxylic acids under bidendate-chelation assistance is developed. This method provides an efficient approach to acyoxy-substituted arenes with a broad range of functional group tolerance. Furthermore, this reaction system could be further applied to the preparation of polyfunctional naphthylenes.

Cobalt-catalyzed, aminoquinoline-directed C(sp2)-H bond alkenylation by alkynes

A method for cobalt-catalyzed, aminoquinoline- and picolinamide-directed C(sp2)-H bond alkenylation by alkynes was developed. The method shows excellent functional-group tolerance and both internal and terminal alkynes are competent substrates for the coupling. The reaction employs a Co(OAc)2·4 H2O catalyst, Mn(OAc)2 co-catalyst, and oxygen (from air) as a terminal oxidant.

Iron-Catalyzed Directed C(sp2)-H and C(sp3)-H Functionalization with Trimethylaluminum

Conversion of a C(sp2)-H or C(sp3)-H bond to the corresponding C-Me bond can be achieved by using AlMe3 or its air-stable diamine complex in the presence of catalytic amounts of an inorganic iron(III) salt and a diphosphine along with 2,3-dichlorobutane as a stoichiometric oxidant. The reaction is applicable to a variety of amide substrates bearing a picolinoyl or 8-aminoquinolyl directing group, enabling methylation of a variety of (hetero)aryl, alkenyl, and alkyl amides. The use of the mild aluminum reagent prevents undesired reduction of iron and allows the reaction to proceed with catalyst turnover numbers as high as 6500.