3864-18-4

Usage

Uses

Used in Catalyst Preparation:
2,3-Dimethylbiphenyl is used as a reagent in the preparation of carbene complexes, which function as catalysts for Suzuki coupling reactions. These reactions are widely employed in the synthesis of various organic compounds, including pharmaceuticals and agrochemicals, due to their ability to form carbon-carbon bonds.
Used in Organic Synthesis:
As an intermediate in organic synthesis, 2,3-Dimethylbiphenyl is utilized in the production of a range of chemical compounds. Its presence in the biphenyl core structure allows for further functionalization and modification, making it a valuable component in the synthesis of various organic molecules.

InChI:InChI=1/C14H14/c1-11-7-6-10-14(12(11)2)13-8-4-3-5-9-13/h3-10H,1-2H3

Upstream product

• 95-47-6 o-xylene 
• 2396-01-2 phenyl radical 
• 87-59-2 2,3-Dimethylaniline 
• 71-43-2 benzene 
• 106-42-3 para-xylene 
• 108-94-1 cyclohexanone 
• 31599-60-7 1-iodo-2,3-dimethylbenzene 
• 98-80-6 phenylboronic acid 
• 576-23-8 2,3-dimethylbromobenzene 
• 2778-58-7 2,3-Dimethylphenyl-p-toluolsulfonat 
• 93-55-0 1-phenyl-propan-1-one 
• 608-23-1 3-chloro-o-xylene 
• 1124-19-2 phenyltin trichloride 
• 220322-94-1 (3,3-dimethylhex-5-en-1-yn-1-yl)benzene 

Relevant academic research and scientific papers

Easily Prepared Mono(N,N-dialkylamino)phosphine Palladium(II) Complexes: Structural and Catalytic Evaluation

The search for efficient, active and universal catalyst systems for transition-metal catalyzed cross-coupling reactions, continues to be of interest to researchers world-wide. Herein, we report two new Pd(II) complexes, effortlessly prepared from N,N-dialkylamino-phosphines for Suzuki-Miyaura cross-coupling reactions. These sufficiently hindered (% VBur=30.0–31.5 %) and electron rich (vCO=1947.41–1946.29 cm?1) aminophosphines formed active catalysts for Suzuki-Miyaura coupling of aryl bromides and chlorides.

A Spiroalkylation Method for the Stereoselective Construction of α-Quaternary Carbons and Its Application to the Total Synthesis of (R)-Puraquinonic Acid

Cyclic α-quaternary carbon stereocenters were prepared from biselectrophillic substrates and an easily prepared chiral bicyclic sulfonyl lactam. This was achieved in two steps by spiroalkylation, employing biphasic reaction conditions with a phase-transfer catalyst, followed by reduction and alkylation with a series of alkyl halide electrophiles. The products of this method were isolated in good yields with with high levels of diastereoselectivity. This methodology was employed in the enantioselective total synthesis of (R)-puraquinonic acid (1) for a late-stage installation of the α-quaternary carbon stereocenter. This enabled the shortest synthesis of 1 to date, an eight-pot sequence providing an overall yield of 14%.

The imidazo{[4,5-f][1,10]-phenanthrolin}l-2-ylidene and its palladium complexes: Synthesis, characterization, and application in C-C cross-coupling reactions

1,3-dibutyl-1H-imidazo[4,5-f][1,10]phenanthrolinium iodide, L5.2HI ligand and their mono-, di-, tri-, tetra-nuclear palladium(II) complexes (5.HPF6, 6–8) were synthesized and characterized by elemental analysis, FTIR, UV–visible and

Development of Structurally Diverse N-Heterocyclic Carbene Ligands via Palladium-Copper-Catalyzed Decarboxylative Arylation of Pyrazolo[1,5-a]pyridine-3-carboxylic Acid

A series of fused non-classical normal N-heterocyclic carbenes, Pyrpy-NHC precursors derived from pyrazolo[1,5-a]pyridines, has been prepared using palladium-copper-catalyzed decarboxylative arylation of pyrazolo[1,5-a]pyridine-3-carboxylic acid. Air-stable palladium and rhodium complexes of these ligands have been synthesized via mild transmetallation of Ag-Pyrpy-NHC. The structural properties of Rh(Pyrpy-NHC)(COD)Cl complexes were determined via X-ray analysis. The measurement of the CO stretching frequencies of dicarbonyl Rh-Pyrpy-NHC complexes revealed that the electron donating strength of Pyrpy-NHC could be tuned by varying the substituents of the aryl group. A catalytic study of the Pd-Pyrpy-NHC complexes revealed promising activity in the Suzuki–Miyaura reaction under ambient atmospheric conditions. (Figure presented.).

Gold(i)-catalyzed dehydrogenative cycloisomerization of 1,5-enynes

The gold(i)-catalyzed dehydrogenative cycloisomerization of cyclopropane-tethered 1,5-enynes proceeded smoothly to give multisubstituted benzene derivatives in good to excellent yields. Synthetically important benzocyclobutenes can be produced in high yields in the presence of a gold(i) catalyst and DDQ. Furthermore, this reaction also works very well for non-cyclopropane tethered 1,5-enynes.

A General Palladium-Catalyzed Hiyama Cross-Coupling Reaction of Aryl and Heteroaryl Chlorides

A general palladium-catalyzed Hiyama cross-coupling reaction of aryl and heteroaryl chlorides with aryl and heteroaryl trialkoxysilanes by a Pd(OAc)2/L2 catalytic system is presented. A newly developed water addition protocol can dramatically improve the product yields. The conjugation of the Pd/L2 system and the water addition protocol can efficiently catalyze a broad range of electron-rich, -neutral, -deficient, and sterically hindered aryl chlorides and heteroaryl chlorides with excellent yields within three hours and the catalyst loading can be down to 0.05 mol % Pd for the first time. Hiyama coupling of heteroaryl chlorides with heteroaryl silanes is also reported for the first time. The reaction can be easily scaled up 200 times (100 mmol) without any degasification and purification of reactants; this facilitates the practical application in routine synthesis.

A 2-methyl-3-phenyl-methanol preparation method

The invention relates to a preparation method of 2-methyl-3-phenyl benzyl alcohol. The preparation method comprises the steps of (1) under a lighting condition, enabling 2,3-dimethyl biphenyl to mix and react with chlorine gas at 40-120 DEGC; or, in the presence of an initiator, enabling the 2,3-dimethyl biphenyl to react with sulfuryl chloride or chlorine gas at 40-120 DEG C; (2) implementing an esterification reaction on 2-methyl-3-chloromethyl biphenyl prepared by the step (1) and an esterification reagent in a solvent in the presence of a catalyst; and (3) under an alkaline condition, hydrolyzing an esterification product prepared by the step (2), and controlling pH range within 9-14. The preparation method disclosed by the invention is simple and convenient to operate, relatively low in cost, not high in requirement on equipment and applicable to industrial production. (img file='DDA0000466672690000011. TIF'wi='1528'he='344'/).

PtI2-catalyzed cyclization of 3-acyloxy-1,5-enynes with the elimination of HOAc and a benzyl shift: Synthesis of unsymmetrical m-terphenyls

A novel cyclization of 3-acyloxy-1,5-enynes is developed in the presence of PtI2 for the synthesis of substituted unsymmetrical m-terphenyls in good to excellent yields. Two unique steps are involved in this transformation, which includes the elimination of HOAc and benzyl group migration. DFT calculations indicated that the rate-determining step is the migration of the benzylic carbocation to form a zwitterionic intermediate followed by the elimination of HOAc. The subsequent cyclopropanation of the zwitterionic intermediate is the regioselectivity-determining step.

Direct catalytic cross-coupling of organolithium compounds

Catalytic carbon-carbon bond formation based on cross-coupling reactions plays a central role in the production of natural products, pharmaceuticals, agrochemicals and organic materials. Coupling reactions of a variety of organometallic reagents and organic halides have changed the face of modern synthetic chemistry. However, the high reactivity and poor selectivity of common organolithium reagents have largely prohibited their use as a viable partner in direct catalytic cross-coupling. Here we report that in the presence of a Pd-phosphine catalyst, a wide range of alkyl-, aryl- and heteroaryl-lithium reagents undergo selective cross-coupling with aryl- and alkenyl-bromides. The process proceeds quickly under mild conditions (room temperature) and avoids the notorious lithium halogen exchange and homocoupling. The preparation of key alkyl-, aryl- and heterobiaryl intermediates reported here highlights the potential of these cross-coupling reactions for medicinal chemistry and material science.

Palladium-catalyzed arylation of simple arenes with iodonium salts

The development of an arylation protocol for simple arenes with diaryliodonium salts using the Herrmann-Beller palladacycle catalyst is reported. The reaction takes simple aromatic feedstocks and creates valuable biaryls for use in all sectors of the chem