1101197-16-3

Upstream product

• 2402-78-0 2,6-dichloropyridine 
• 329685-40-7 4,4,5,5-tetramethyl-2-(3-phenylpropyl)-[1,3,2]dioxaborolane 
• 108-48-5 2,6-dimethylpyridine 
• 100-42-5 styrene 
• 100-52-7 benzaldehyde 
• 1124-74-9 2,6-divinylpyridine 
• 5281-18-5 benzaldehyde, hydrazone 
• 626-05-1 2,6-Dibromopyridine 
• 637-59-2 1-Bromo-3-phenylpropane 

Downstream Products

• 1101197-08-3 C₂₃H₃₁N 

Relevant academic research and scientific papers

Yttrium-catalyzed addition of benzylic C-H bonds of alkyl pyridines to olefins

Cationic half-sandwich yttrium alkyl complexes catalyze the ortho-selective benzylic C-H addition of dialkyl pyridines to various olefins, such as ethylene, 1-hexene, styrenes, and 1,3-conjugated dienes, to afford new alkylated and allylated pyridine derivatives (see scheme; Cp=C5Me 5). A cationic half-sandwich yttrium picolyl species, such as [CpY(2-CH2-6-CH3C5H3N)] +, has been confirmed to be a key active species in this transformation. Copyright

Calcium-mediated C(sp3)-H Activation and Alkylation of Alkylpyridines

Main-group metal calcium-mediated alkylpyridine benzylic C(sp3)-H activation and functionalization have been achieved. The reaction of a calcium hydride complex [{(DIPPnacnac)CaH(thf)}2] (DIPPnacnac = CH{(CMe)(2,6-iPr2-C6H3N)}2) with two equivalents of 2,6-lutidine rapidly yields a monomeric calcium alkyl complex with the release of dihydrogen. A hydride/carbon-bridged binuclear calcium complex [{(DIPPnacnac)Ca}2(μ-H){2-Me-6-(μ-CH2)-Py}(thf)] is obtained from an equimolar treatment of calcium hydride and 2,6-lutidine that is readily converted into mono- or binuclear calcium alkyl complexes upon subsequent addition of 2,6-lutidine. DFT calculations and kinetic studies are conducted to determine their reaction profiles. More significantly, this calcium hydride complex catalyzes regioselective benzylic C-H bond addition of alkylpyridines to a variety of alkenes, affording linear or branched alkylated pyridine derivatives.

Ruthenium catalyzed β-selective alkylation of vinylpyridines with aldehydes/ketonesviaN2H4mediated deoxygenative couplings

Umpolung (polarity reversal) tactics of aldehydes/ketones have greatly broadened carbonyl chemistry by enabling transformations with electrophilic reagents and deoxygenative functionalizations. Herein, we report the first ruthenium-catalyzed β-selective alkylation of vinylpyridines with both naturally abundant aromatic and aliphatic aldehyde/ketonesviaN2H4mediated deoxygenative couplings. Compared with one-electron umpolung of carbonyls to alcohols, this two-electron umpolung strategy realized reductive deoxygenation targets, which were not only applicable to the regioselective alkylation of a broad range of 2/4-alkene substituted pyridines, but also amenable to challenging 3-vinyl and steric-embedded internal pyridines as well as their analogous heterocyclic structures.

Tris(benzhydryl) and Cationic Bis(benzhydryl) Ln(III) Complexes: Exceptional Thermostability and Catalytic Activity in Olefin Hydroarylation and Hydrobenzylation with Substituted Pyridines

A series of Ln(III) tris(benzhydryl) complexes [(p-tBu-C6H4)2CH]3Ln (Ln=La (1), Nd (2), Y (3)) were synthesized by the salt metathesis reactions of LnHal3(THF)3.5 (Ln=La, Nd, Hal=Cl; Ln=Y, Hal=I) and [(p-tBu-C6H4)2CH]Na. In 1–3 the benzhydryl ligands are linked with the metal centres in η4-coordination mode. For diamagnetic complexes 1 and 3 a fluxional behaviour was detected in solution. Complexes 1–3 proved to be thermally stable: no decomposition was observed even after heating their solutions in toluene-d8 at 140 °C during 72 h. The reactions of 1 and 2 with B(C6F5)3 allowed for the synthesis of base-free cationic complexes [(p-tBu-C6H4)2CH]2Ln[(p-tBu-C6H4)2CHB(C6F5)3] (Ln=La (4), Nd (5)) which adopt the structure of a contact ion pair. Combinations of 1–3 and borane ((B(C6F5)3, [Me2NHPh][B(C6F5)4], [Ph3C][B(C6F5)4]) as well as 4 and 5 were found to be highly efficient, regio- and chemoselective catalysts for hydroarylation and hydrobenzylation of C=C bonds of a variety of substrates with substituted pyridines. These catalysts enable highly challenging transformations such as hydrobenzylation of 1,1-disubstituted and internal C=C bonds. (Figure presented.).

Exhaustive Suzuki-Miyaura reactions of polyhalogenated heteroarenes with alkyl boronic pinacol esters

A novel Suzuki-Miyaura protocol is described that enables the exhaustive alkylation of polychlorinated pyridines. This method facilitates a formal synthesis of normuscopyridine and the rapid assembly of a dumbbell shaped portion of a [2]rotaxane.

Selective and Serial Suzuki-Miyaura Reactions of Polychlorinated Aromatics with Alkyl Pinacol Boronic Esters

Among cross-coupling reactions, the Suzuki-Miyaura transformation stands out because of its practical advantages, including the commercial availability and low toxicity of the required reagents, mild reaction conditions, and functional group compatibility. Nevertheless, few conditions can be used to cross-couple alkyl boronic acids or esters with aryl halides, especially 2-pyridyl halides. Herein, we describe two novel Suzuki-Miyaura protocols that enable selective conversion of polychlorinated aromatics, with a focus on reactions to convert 2,6-dichloropyridines to 2-chloro-6-alkylpyridines or 2-aryl-6-alkylpyridines.

Synthesis and evaluation of a series of homologues of lobelane at the vesicular monoamine transporter-2

A series of lobelane homologues has been synthesized and evaluated for their [3H]DTBZ binding affinity at the vesicular monoamine transporter-2 (VMAT2). The structure-activity relationships (SAR) indicate that for retention of binding affinity at VMAT2, the lengths of the methylene linkers should be no shorter than one methylene unit at C-6 of the piperidine ring, and no shorter than two methylene units at C-2 of the piperidine ring. These results indicate that the intramolecular distances between the piperidine ring and two phenyl rings in lobelane analogues are an important criterion for retention of high affinity at VMAT2.