320369-29-7

Upstream product

• 92-91-1 biphenyl-4-acetaldehyde 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 

Downstream Products

• 2350-89-2 p-vinylbiphenyl 
• 1373368-70-7 2-(4-phenylphenyl)-1-phenylprop-2-enone 
• 38922-75-7 2-([1,1'-biphenyl]-4-yl)imidazo[1,2-a]pyridine 
• 64273-27-4 4-([1,1′-biphenyl]-4-yl)-1,2,3-thiadiazole 
• 67362-98-5 2-([1,1′-biphenyl]-4-yl)benzo[d]thiazole 

Relevant academic research and scientific papers

Aryl-Diadamantyl Phosphine Ligands in Palladium-Catalyzed Cross-Coupling Reactions: Synthesis, Structural Analysis, and Application

Synthesis, temperature-dependent NMR structure investigation and utilization of a new, stable and easily accessible aryl-diadamantylphosphine ligand family is reported. The bulky and electron-rich phosphorus center of the ligand enhances the catalytic activity of palladium in cross-coupling reactions of sterically demanding ortho-substituted aryl halides. In our study, we demonstrated the synthetic applicability of the new phosphine ligands in Buchwald-Hartwig and tosyl hydrazone coupling reactions.

Umpolung Difunctionalization of Carbonyls via Visible-Light Photoredox Catalytic Radical-Carbanion Relay

The combination of photoredox catalysis with the Wolff-Kishner (WK) reaction allows the difunctionalization of carbonyl groups by a radical-carbanion relay sequence (photo-Wolff-Kishner reaction). Photoredox initiated radical addition to N-sulfonylhydrazones yields α-functionalized carbanions following the WK-type mechanism. With sulfur-centered radicals, the carbanions are further functionalized by reaction with electrophiles including CO2 and aldehydes, whereas CF3 radical addition furnishes a wide range of gem-difluoroalkenes through β-fluoride elimination of the generated α-CF3 carbanions. More than 80 substrate examples demonstrate the broad applicability of this reaction sequence. A series of investigations including radical inhibition, deuterium labeling, fluorescence quenching, cyclic voltammetry, and control experiments support the proposed radical-carbanion relay mechanism.

Pyrrolo-imidazo[1,2- A[pyridine Scaffolds through a Sequential Coupling of N-Tosylhydrazones with Imidazopyridines and Reductive Cadogan Annulation, Synthetic Scope, and Application

A new strategy for the construction of 3-phenyl-1H-pyrrolo-imidazo[1,2-a]pyridine backbone is described. The reaction starts from the coupling between N-tosylhydrazones and 2-chloro-3-nitroimidazo[1,2-a]pyridines leading to the formation of 3-nitro-2-(ary

Synthesis of Multi-substituted Dihydropyrazoles by Copper-Mediated [4+1] Cycloaddition Reaction of N-Sulfonylhydrazones and Sulfoxonium Ylides

A general and expeditious approach for the copper mediated synthesis of multi-functionalized dihydropyrazoles from N-sulfonylhydrazones and sulfoxonium ylides has been achieved under aerobic oxidative conditions. The formal [4+1] cycloaddition reaction ex

Selective Construction of 2-Substituted Benzothiazoles from o-Iodoaniline Derivatives S8 and N-Tosylhydrazones

Selective construction of 2-substituted benzothiazoles from o-iodoaniline derivatives S8 and N-tosylhydrazone via a copper-promoted [3 + 1 + 1]-type cyclization reaction has been realized. In the protocol, the carbon atom on N-tosylhydrazone could be regulated to construct benzothiazole by changing the reaction system. Furthermore, the transformation has achieved the construction of multiple carbon-heteroatom bonds.

Rhodium-Catalyzed B-H Bond Insertion Reactions of Unstabilized Diazo Compounds Generated in Situ from Tosylhydrazones

Although transition-metal-catalyzed B-H bond insertion of carbenes into stable borane adducts has emerged as a promising method for organoborane synthesis, all the diazo compounds used to date as carbene precursors have had an electron-withdrawing group to stabilize them. Herein, we report a protocol for rhodium-catalyzed B-H bond insertion reactions of unstabilized diazo compounds generated in situ from tosylhydrazones. In addition, by using chiral dirhodium catalysts, we also achieved an asymmetric version of the reaction with good to excellent enantioselectivities (up to 98:2 e.r.). This is the first enantioselective heteroatom-hydrogen bond insertion reaction to use unstabilized diazo compounds as carbene precursors. The protocol exhibited good functional group tolerance and could be carried out on a gram scale. It also enabled one-pot transformation of a carbonyl group to a boryl group enantioselectively. The B-H bond insertion products could be easily transformed into chiral alcohols and other widely used organoboron reagents with enantiomeric fidelity.

One-pot reductive coupling reactions of acetyl naphthalene derivatives, tosylhydrazide, with arylboronic acids

In this study, a one-pot two-step reductive coupling between acetyl naphthalene derivatives, tosylhydrazide, and arylboronic acids, affording substituted 1(or 2)-(1-phenylethyl)naphthalenes in moderate-to-excellent yields, was reported. Notably, solvent played a crucial role in the coupling of 1-acetyl naphthalene derivatives (toluene) or 2-acetyl naphthalene derivatives (1,4-dioxane) as starting materials. Meanwhile, the scope of this one-pot coupling reaction was extended to 1(or 2)-naphthaldehyde substrates. Particularly, the system was also suitable to synthesize 1(or 2)-(1-phenylethyl)naphthalenes on a multi-gram scale, and was applied in the synthesis of naphthylmethyl substituted carbazolyl compounds.

Pd(0)-Catalyzed Tandem One-Pot Reaction of Biphenyl Ketones/Aldehydes to the Corresponding Di-substituted Aryl Olefins

Synthesis of di-substituted aryl olefins via a Pd(0)-catalyzed cross-coupling reaction of biphenyl ketones/aldehydes, tosylhydrazide, and aryl bromides (or benzyl halides) was developed. This methodology was achieved by one-pot two-step reactions involvin

Palladium-Catalyzed One-Pot Synthesis of 5-(1-Arylvinyl)-1H-benzimidazoles: Overcoming the Limitation of Acetamide Partners

A new one-pot palladium-catalyzed process between N-tosylhydrazones, N-(dihalophenyl)-imidates, and amines was designed. This reaction involves Barluenga cross-coupling and N-arylation followed by cyclization to produce functionalized benzimidazoles. Duri

Copper-Mediated [3 + 2] Oxidative Cyclization Reaction of N-Tosylhydrazones and β-Ketoesters: Synthesis of 2,3,5-Trisubstituted Furans

The first attempt at utilizing N-tosylhydrazones as two-carbon synthons has been successfully achieved, which underwent a copper-mediated [3 + 2] oxidative cyclization reaction to afford 2,3,5-trisubstituted furans in moderate to good yields. The features of this method include inexpensive metal catalyst, readily available substrates, high regioselectivity, and convenient operation. The studies provide important approaches for further exploration of the powerful and diverse reaction abilities of N-tosylhydrazones.