3678-70-4

Usage

Chemical Properties

light yellow-orange cryst. powder and crystals

InChI:InChI=1/C18H15N/c1-3-9-15(10-4-1)18(16-11-5-2-6-12-16)17-13-7-8-14-19-17/h1-14,18H

Upstream product

• 109-06-8 α-picoline 
• 108-90-7 chlorobenzene 
• 19490-90-5 diphenyl(2-pyridyl)methanol 
• 29958-04-1 2-(2-chloro-1,1-diphenylethyl)pyridine 
• 1121-60-4 pyridine-2-carbaldehyde 
• 71-43-2 benzene 
• 86-29-3 Diphenylacetonitrile 
• 31796-72-2 phenyl(2-pyridinyl)methanol 
• 98-80-6 phenylboronic acid 
• 832-81-5 3-phenyl-[1,2,3]triazolo[1,5-a]pyridine 
• 109-04-6 2-bromo-pyridine 
• 139-66-2 diphenyl sulfide 
• 100-68-5 methyl-phenyl-thioether 
• 2459-07-6 methyl pyridine-2-carboxylate 

Downstream Products

• 29958-04-1 2-(2-chloro-1,1-diphenylethyl)pyridine 
• 109975-56-6 2-(4-methylphenyl)-1,1-diphenyl-1-(2-pyridyl)ethane 
• 106109-15-3 [Pd((C₅H₄N)(C₆H₅)2CH)2(CH₃COO)2] 
• 79043-58-6 (diphenyl(2-pyridyl)methane)methylmercury(II) nitrate 
• 1047650-76-9 (2-butylphenyl)phenyl-2-pyridylmethane 
• 33583-12-9 10-phenylpyrido[1,2-a]indole 
• 19490-90-5 diphenyl(2-pyridyl)methanol 
• 97573-56-3 1-allyl-2-benzhydryl-piperidine 
• 1916-50-3 2-benzhydrylidene-1-methyl-1,2-dihydro-pyridine 
• 149091-02-1 lithium diphenyl-2-pyridylmethanethiolate 
• 130710-20-2 2-(Dichlorosilanyl-diphenyl-methyl)-pyridine 
• 130710-21-3 2-[(Dichloro-methyl-silanyl)-diphenyl-methyl]-pyridine 
• 519-74-4 2-(diphenylmethyl)piperidine 

Relevant academic research and scientific papers

Synthesis of Triarylmethanes via Palladium-Catalyzed Suzuki-Miyaura Reactions of Diarylmethyl Esters

The synthesis of triarylmethanes via Pd-catalyzed Suzuki-Miyaura reactions between diarylmethyl 2,3,4,5,6-pentafluorobenzoates and aryl boronic acids is described. The system operates under mild conditions and has a broad substrate scope, including the coupling of diphenylmethanol derivatives that do not contain extended aromatic substituents. This is significant as these substrates, which result in the types of triarylmethane products that are prevalent in pharmaceuticals, have not previously been compatible with systems for diarylmethyl ester coupling. Furthermore, the reaction can be performed stereospecifically to generate stereoinverted products. On the basis of DFT calculations, it is proposed that the oxidative addition of the diarylmethyl 2,3,4,5,6-pentafluorobenzoate substrate occurs via an SN2 pathway, which results in the inverted products. Mechanistic studies indicate that oxidative addition of the diarylmethyl 2,3,4,5,6-pentafluorobenzoate substrates to (IPr)Pd(0) results in the selective cleavage of the O-C(benzyl) bond in part because of a stabilizing η3-interaction between the benzyl ligand and Pd. This is in contrast to previously described Pd-catalyzed Suzuki-Miyaura reactions involving phenyl esters, which involve selective cleavage of the C(acyl)-O bond, because there is no stabilizing η3-interaction. It is anticipated that this fundamental knowledge will aid the development of new catalytic systems, which use esters as electrophiles in cross-coupling reactions.

Light-induced metal-free transformations of unactivated pyridotriazoles

A highly efficient and practical method for incorporation of the arylmethylpyridyl moiety into diverse molecules has been developed. This method features the transition metal-free light-induced room temperature transformation of pyridotriazoles into pyridyl carbenes, which are capable of smooth arylation, X-H insertion, and cyclopropanation reactions. The synthetic usefulness of the developed method was illustrated in a facile synthesis of biologically active molecules.

Directed: Ortho C-H borylation catalyzed using Cp?Rh(iii)-NHC complexes

Cp?Rh(NHC) complexes with bulky chiral bidentate NHC-carboxylate ligands were efficiently synthesized and fully characterized including solid-state structures. These unprecedented rhodium(iii) complexes demonstrated high selectivity in pyridine-directed ortho-C-H borylation of arenes under mild conditions.

An Unprecedented Family of Luminescent Iridium(III) Complexes Bearing a Six-Membered Chelated Tridentate C^N^C Ligand

A new family consisting of three luminescent neutral Ir(III) complexes with the unprecedented [Ir(C^N^C)(N^N)Cl] architecture, where C^N^C is a bis(six-membered) chelating tridentate tripod ligand derived from 2-benzhydrylpyridine (bnpy) and N^N is 4,4′-di-tert-butyl-2,2′-bipyridine (dtBubpy), is reported. X-ray crystallography reveals an unexpected and unusual double C-H bond activation of the two distal nonconjugated phenyl rings of the bnpy coupled with a very short Ir-Cl bond trans to the pyridine of the bnpy ligand. Depending on the substitution on the bnpy ligand, phosphorescence, ranging from yellow to red, is observed in dichloromethane solution. A combined study using density functional theory (DFT) and time-dependent DFT (TD-DFT) corroborates the mixed charge-transfer nature of the related excited states.

Palladium-Catalyzed Arylation of Benzylic C-H Bonds of Azaarylmethanes with Aryl Sulfides

Benzylic C-H arylation of azaarylmethanes with aryl sulfides has been developed by using a Pd-NHC catalyst and an amide base. Various azaarylmethanes and aryl sulfides were involved in the reaction to afford the corresponding diarylmethanes in good to excellent yields. Moreover, triarylmethane synthesis was accomplished through iterative arylations of 2- or 4-methylpyridine with two different aryl sulfides.

Nickel-catalyzed arylation of heteroaryl-containing diarylmethanes: Exceptional reactivity of the Ni(NIXANTPHOS)-based catalyst

Nickel(0)-catalyzed cross-coupling of heteroaryl-containing diarylmethanes with both aryl bromides and chlorides has been achieved. The success of this reaction relies on the introduction of a unique nickel/NIXANTPHOS-based catalyst system, which provides a direct route to triarylmethanes from heteroaryl-containing diarylmethanes. Reactivity studies indicate the Ni(NIXANTPHOS)-based catalyst exhibits enhanced reactivity over XANTPHOS derivatives and other Ni(phosphine)-based catalysts in the reactions examined.

Rh(I)/NHC*-Catalyzed site- and enantioselective functionalization of c(sp3)?H bonds toward chiral triarylmethanes

The first Rh(I)-catalyzed asymmetric approach for the intermolecular functionalization of C(sp3)?H bonds is reported. For the first time, unsymmetrical N-heterocyclic carbenes (NHCs) were used for asymmetric catalysis that is capable of achieving not only high site-selectivity but also enantioselectivity. The Rh(I)/NHC* catalytic systems were applied to asymmetric direct C(sp3)?H arylation, which provides a synthetic route toward enantioenriched triarylmethanes.

LDA-Mediated Synthesis of Triarylmethanes by Arylation of Diarylmethanes with Fluoroarenes at Room Temperature

A practical and convenient approach for the secondary C(sp3)-H arylation of diarylmethanes with various fluoroarenes is described. The reaction proceeds smoothly in the presence of LDA (lithium diisopropylamide) at room temperature and affords triarylmethanes in moderate to high yields.

Iron-catalyzed C-H bond functionalization for the exclusive synthesis of pyrido[1,2-a]indoles or triarylmethanols

The efficient and selective iron-catalyzed C-H activation of 2-benzhydrylpyridine derivatives was employed for the preparation of pyrido[1,2-a]indoles through an intramolecular C-H amination reaction. In the presence of molecular oxygen as the sole oxidant, the same 2-benzhydrylpyridines were also used for the synthesis of the corresponding tertiary alcohols. In these approaches, the iron catalyst was used to selectively activate the C(sp2)-H bond of 2-benzhydrylpyridine, in the case of the intramolecular ring-closing C-H amination reaction in which the pyridine nitrogen atom was a directing group as well as a nucleophile, and the C(sp3)-H bond of the same compound, in the case of the oxidation reaction to give the corresponding triaryl carbinol.

Additive effects on palladium-catalyzed deprotonative-cross-coupling processes (DCCP) of sp3 C-H bonds in diarylmethanes

Palladium-catalyzed cross-coupling reactions have become one of the most useful tools in modern organic chemistry. Current methods to achieve direct functionalization of sp3 C-H bonds of arenes and heteroarenes often employ substrates with appropriately placed directing groups to enable reactivity. Examples of intermolecular arylation methods of weakly acidic sp3 C-H bonds in the absence of directing groups, however, are still limited. We describe herein a study on the use of additives in Pd-catalyzed deprotonative-cross-coupling processes (DCCP) of sp3 C-H bonds of diarylmethanes with aryl bromides at room temperature. These studies resulted in development of four new efficient Pd-catalyzed DCCP using additives that enabled the generation of a range of sterically and electronically diverse aryl- and heteroaryl containing triarylmethanes in good to excellent yields. Additive identification and optimization of all reaction conditions (additive loading, solvent and temperature) were performed using high-throughput experimentation (HTE). The approach outlined herein is expected to be generalizable to other C-H functionalization reactions involving the deprotonation of weakly acidic C-H bonds. The Royal Society of Chemistry 2013.