134616-36-7

Upstream product

• 100-48-1 pyridine-4-carbonitrile 
• 98-73-7 4-(1,1-dimethylethyl)benzoic acid 
• 127349-68-2 (4-(tert-butyl)benzyl)magnesium bromide 
• 63755-30-6 N-ethoxycarbonylpyridinium chloride 

Relevant academic research and scientific papers

Metal-Free Heterogeneous Semiconductor for Visible-Light Photocatalytic Decarboxylation of Carboxylic Acids

A suitable protocol for the photocatalytic decarboxylation of carboxylic acids was developed with metal-free ceramic boron carbon nitrides (BCN). With visible light irradiation, BCN oxidize carboxylic acids to give carbon-centered radicals, which were trapped by hydrogen atom donors or employed in the construction of the carbon-carbon bond. In this system, both (hetero)aromatic and aliphatic acids proceed the decarboxylation smoothly, and C-H, C-D, and C-C bonds are formed in moderate to high yields (35 examples, yield up to 93%). Control experiments support a radical process, and isotopic experiments show that methanol is employed as the hydrogen atom donor. Recycle tests and gram-scale reaction elucidate the practicability of the heterogeneous ceramic BCN photoredox system. It provides an alternative to homogeneous catalysts in the valuable carbon radical intermediates formation. Moreover, the metal-free system is also applicable to late-stage functionalization of anti-inflammatory drugs, such as naproxen and ibuprofen, which enrich the chemical toolbox.

Light-Induced Alkylation of (Hetero)aromatic Nitriles in a Transition-Metal-Free C-C-Bond Metathesis

A light-induced C-C-σ-bond metathesis was achieved through transition-metal-free activation of an unstrained C(sp3)-C(sp3)-σ-bond in 1-benzyl-1,2,3,4-tetrahydroisoquinolines. A photoredox-mediated single-electron oxidation of these precursor amines yield radical cations which undergo a homolytic cleavage of a C(sp3)-C(sp3)-σ-bond rather than the well-known α-C-H-scission. The resulting carbon-centered radicals are used in the ipso-substitution of (hetero)aromatic nitriles proceeding through another single-electron transfer-mediated C-C-bond cleavage and formation.

A facile synthesis of functionalized 4-benzylpyridines by using mixed copper, zinc benzylic organometallics

A general approach by use of highly functionalized mixed copper zinc, benzylic organometallics to react with N-ethoxycarbonylpyridinium chloride to give regioselectively 4-benzylpyridines after oxygen oxidation in 30-75% yield is described.

A facile synthesis of 4-benzylpyridines by regiospecific addition of substituted benzylic Griganard reagents to pyridinium salts

Substituted 4-benzylpyridines are prepared by regiospecific γ-addition of substituted benzylic Grinard reagents to pyridinium salts in fairly good yields.