99159-24-7

Upstream product

• 98437-23-1 benzo[b]thiophene-2-boronic acid 
• 91-01-0 1,1-Diphenylmethanol 
• 5433-76-1 diphenylmethyl phenyl sulfone 
• 95-15-8 Benzo[b]thiophene 
• 5670-78-0 ethyl diphenylmethyl ether 
• 954-67-6 benzhydryl acetate 
• 19672-37-8 3-benzhydryl-pentane-2,4-dione 

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.

Synthesis of Triarylmethanes via Palladium-Catalyzed Suzuki Coupling of Trimethylammonium Salts and Arylboronic Acids

An efficient palladium-catalyzed Suzuki coupling of 1,1-diarylmethyl-trimethylammonium triflates with arylboronic acids is reported. This reaction offers a novel approach to triarylmethane derivatives in good to excellent yields with the palladium-catalyzed C-N bond cleavage as the key feature. Broad substrate scope regarding both reaction partners are observed. Moreover, reactive functional groups such as vinyl and formyl groups are conserved in this transformation.

Phosphomolybdic acid as a bifunctional catalyst for Friedel–Crafts type dehydrative coupling reaction

Phosphomolybdic acid (H3PMo12O40) was found to be a bifunctional catalyst for C─C bond formation via the dehydrative reaction of diarylmethanols with various nucleophiles, including 2-naphthols, indoles, benzofuran and ben

Arylative Desulfonation of Diarylmethyl Phenyl Sulfone with Arenes Catalyzed by Scandium Triflate

A scandium-triflate-catalyzed arylative desulfonation of diarylmethyl phenyl sulfones with arenes and heteroarenes was established. A variety of both sulfone and arene substrates were reacted to afford symmetric and nonsymmetric triarylmethanes in good yields. Further transformations of the resulting triarylmethanes and application to the concise synthesis of a bactericidal agent analogue were also demonstrated.

Copper-mediated arylation with arylboronic acids: Facile and modular synthesis of triarylmethanes

A facile and modular synthesis of triarylmethanes was achieved in good yield via a two-step sequence in which the final step is the copper(II)-catalyzed arylation of diarylmethanols with arylboronic acids. By using this protocol a variety of symmetrical and unsymmetrical triarylmethanes were synthesized. As an application of the newly developed methodology, we demonstrate a highyielding synthesis of the triarylmethane intermediate towards an anti-breast-cancer drug candidate.

Simple Method for sp2-sp3 and sp3-sp3 Carbon-Carbon Bond Activation in 2-Substituted 1,3-Diketones

Simple and efficient methods were developed for sp2-sp3 and sp3-sp3 C-C bond-activation reactions of 2-substituted 1,3-diketones. 3-Substituted 3-bromopentane-2,4-diones were deacylated in the presence of an aromatic compound and a silica gel supported Bronsted acid containing sulfonic groups. The carbocation formed by cleavage of the sp3-sp3 C-C bond of the dione alkylated the aromatic compound.

Direct alkylation of aromatics using alcohols in the presence of NaHSO 4/SiO2

Simple and efficient procedure for alkylation of aromatics from alcohols in the presence of NaHSO4/SiO2 was developed. Various triaryl methanes were obtained in good yields in short reaction time. For instance the reaction of mesitylene with benzhydrol in the presence of NaHSO4/SiO2 gave the corresponding triaryl methane in a quantitative yield. NaHSO4/SiO2 was regenerated by simple treatment and could be recycled eight times without activity loss.

First example of a heterobimetallic 'Pd-Sn' catalyst for direct activation of alcohol: Efficient allylation, benzylation and propargylation of arenes, heteroarenes, active methylenes and allyl-Si nucleophiles

Arenes, heteroarenes, 1,3-dicarbonyls and organosilicon nucleophiles undergo highly efficient alkylation with allylic, propargylic and benzylic alcohols in the presence of a new 'Pd-Sn' bimetallic catalyst in nitromethane; water being the sole byproduct.

PdCl2-catalyzed efficient allylation and benzylation of heteroarenes under ligand, base/acid, and additive-free conditions

We present a PdCl2-catalyzed protocol for highly efficient allylation and benzylation of a rich variety of N-, O-, and S-containing heteroarenes under base/acid, additive, and ligand-free conditions. The method represents the very few examples