1332460-91-9

Upstream product

• 1008-89-5 2-phenylpyridine 
• 110-82-7 cyclohexane 
• 4441-56-9 cyclohexylboronic acid 
• 1131-33-5 2-phenylpyridin N-oxide 
• 2043-61-0 cyclohexanecarbaldehyde 
• 1005135-44-3 2-phenyl-N-benzoyliminopyridinium ylide 

Relevant academic research and scientific papers

Regio- and Stereoselective Alkylation of Pyridine-N-oxides: Synthesis of Substituted Piperidines and Pyridines

Regio- and stereoselective addition of alkyl Grignard reagents to pyridine-N-oxides gave C2-alkylated N-hydroxy-1,2,5,6-tetrahydropyridines and trans-2,3-disubstituted N-hydroxy-1,2,5,6-tetrahydropyridines in good to excellent yields. These intermediates were aromatized or alternatively reduced in one-pot methodologies for efficient syntheses of alkylpyridines or piperidines, respectively. These reactions have a broad substrate scope and short reaction times.

Visible-light-mediated photoredox minisci C-H alkylation with alkyl boronic acids using molecular oxygen as an oxidant

Herein, we report a protocol for direct visible-light-mediated Minisci C-H alkylation reactions of heteroarenes with alkyl boronic acids using molecular oxygen as the sole oxidant. This mild protocol uses an inexpensive, green oxidant; permits efficient functionalization of various N-heteroarenes with a broad range of primary and secondary alkyl boronic acids; and is scalable to the gram level. We demonstrated the practicality and sustainability of the protocol by preparing or functionalizing several pharmaceuticals and natural products.

Metal-Free Oxidative Decarbonylative Coupling of Aliphatic Aldehydes with Azaarenes: Successful Minisci-Type Alkylation of Various Heterocycles

A metal-free oxidative decarbonylative coupling of aliphatic aldehydes with various electron-deficient heterocycles has been developed. This reaction is supposed to be realized via a Minisci-type mechanism, based on the substrate scope, regioselectivity and radical trapping experiments. The ready availability of aliphatic aldehydes, metal-free conditions and broad substrate scope should make this method attractive for the late-stage alkylation of bioactive heterocycles.

Benzoyl peroxide promoted radical ortho-alkylation of nitrogen heteroaromatics with simple alkanes and alcohols

A catalytic amount of benzoyl peroxide (BPO)-initiated cross-dehydrogenative coupling reaction of N-iminopyridine ylides with simple alkanes and alcohols leads to the corresponding 2-alkylpyridines with high regioselectivity in moderate to good yields without an additional reduction step to remove the activated group. A catalytic amount of benzoyl peroxide (BPO)-initiated cross-dehydrogenative coupling reaction of N-iminopyridine ylides with simple alkanes and alcohols has been developed. The strategy allowed convenient access to various 2-alkylpyridines in moderate to good yields without an additional reduction step to remove the activated group.

Ruthenium-catalyzed para-selective oxidative cross-coupling of arenes and cycloalkanes

A novel, direct para-selective oxidative cross-coupling of benzene derivatives with cycloalkanes catalyzed by ruthenium was developed. A wide range of arenes bearing electron-withdrawing substituents was functionalized directly with simple cycloalkanes with high para-selectivity; arenes with electron-donating groups were mainly para-functionalized. Benzoic acid can be used directly.