167847-61-2

Upstream product

• 14003-16-8 5-methylfurfurylamine 
• 98-59-9 p-toluenesulfonyl chloride 
• 70-55-3 toluene-4-sulfonamide 
• 620-02-0 5-Methylfurfural 
• 463352-90-1 4-methyl-N-[(5-methylfuran-2-yl)methylene]benzenesulfonamide 

Downstream Products

• 317834-47-2 4-methyl-N-[(5-methylfuran-2-yl)methyl]-N-(prop-2-yne-1-yl)benzenesulfonamide 
• 1310361-67-1 3-(2-ethenylphenyl)-5-methyl-2-[(4-methylphenyl)sulfonyl]-2,3-dihydro-1H-isoindol-4-ol 
• 1393117-30-0 5-methyl-2-[(4-methylphenyl)sulfonyl]-7-(4-nitrophenyl)-2,3-dihydro-1H-isoindol-4-ol 
• 1393117-29-7 5-methyl-2-[(4-methylphenyl)sulfonyl]-7-(3-nitrophenyl)-2,3-dihydro-1H-isoindol-4-ol 
• 1393117-28-6 7-(3-methoxyphenyl)-5-methyl-2-[(4-methylphenyl)sulfonyl]-2,3-dihydro-1H-isoindol-4-ol 
• 1393117-27-5 7-iodo-5-methyl-2-[(4-methylphenyl)sulfonyl]-2,3-dihydro-1H-isoindol-4-ol 
• 1393117-26-4 7-chloro-5-methyl-2-[(4-methylphenyl)sulfonyl]-2,3-dihydro-1H-isoindol-4-ol 
• 1393117-17-3 7-bromo-5-methyl-2-[(4-methylphenyl)sulfonyl]-2,3-dihydro-1H-isoindol-4-ol 

Relevant academic research and scientific papers

Water Can Accelerate Homogeneous Gold Catalysis

A selection of gold-catalyzed reactions was examined in a kinetic study on the influence of water on the rate constant. Two intramolecular reactions and one intermolecular reaction, which proceed via proton transfer and/or protodeauration steps, were inve

Heterogeneous gold-catalysed synthesis of phenols

Nanoparticles of gold supported on nanocrystalline CeO2 catalyse the isomerisation of ω-alkynylfurans to phenols. Initial leaching of gold was observed, which could be minimised by calcining. Subsequent runs showed that once all soluble species

From Furan-Yne Systems to para -Benzoquinone Derivatives: Gold-Catalyzed Cyclization and Oxidation, and Further Reduction by Sodium Dithionate

A series of furan-yne systems were transformed into the corresponding para -benzoquinone derivatives by gold(ΙΙΙ) catalyst. The two-step procedure consisted of a phenol synthesis and subsequent oxidation with iodobenzene diacetate. The reactions can be carried out in a one-pot procedure with the same precatalyst. The para -benzoquinone could simply be converted into the corresponding hydroquinones by reduction with sodium dithionate. This protocol features high efficiency, mild conditions, and wide substrate scopes.

Manganese=Catalyzed Achmatowicz Rearrangement Using Green Oxidant H2O2

Oxidation reactions have been extensively studied in the context of the transformations of biomass=derived furans. However, in contrast to the vast literature on utilizing the stoichiometric oxidants, such as m=CPBA and NBS, catalytic methods for the oxidative furan=recyclizations remain scarcely investigated. Given this, we report a means of manganese=catalyzed oxidations of furan with low loading, achieving the Achmatowicz rearrangement in the presence of hydrogen peroxide as an environmentally benign oxidant under mild conditions with wide functional group compatibility.

Gold(I) Complexes with Eight-Membered NHC Ligands: Synthesis, Structures and Catalytic Activity

A series of expanded-ring NHC gold complexes of the formula (NaphtDHD?Ar)Au?X (NaphtDHD=4,5-dihydro-1H-naphtho[1,8-ef][1,3]diazocin-3(2H)-ylidene; Ar: Mes=2,4,6-trimethylphenyl, Dipp=2,6-diisopropylphenyl or Xyl=2,6-dimethylphenyl; X=Cl, NCCH3, NTf2) have been synthesized, including the first gold(I) triflimidate complex (5) stabilized by an eight-membered NHC ligand. The new organogold compounds have been characterized by mass spectrometry, IR spectroscopy, and 1H and 13C NMR spectroscopy. The structural geometries of 3 b–c and 5 have been unequivocally established by crystallographic analysis revealing broad N-C-N angles (>121°) and high buried volume values (46–54%). The first catalytic studies were carried out on the cycloisomerization of 1,6-enynes, obtaining full conversions (0.5 mol% catalyst loading) and excellent endo/exo selectivity (up to 99:1), and on the gold-catalyzed phenol synthesis. Lastly, the (NaphtDHD-Dipp)Au+ NTf2? species was subjected to a kinetic experiment in the cyclization of a N-propargyl carboxamide to evaluate the efficiency of the pre-formed catalyst (5) and the in situ activated gold complex (3 b+AgNTf2). (Figure presented.).

Divergent gold-catalysed reactions of cyclopropenylmethyl sulfonamides with tethered heteroaromatics

Cyclopropenylmethyl sulfonamides with tethered heteroaromatics have been demonstrated to undergo divergent gold-catalysed cyclisation reactions. A formal dearomative (4+3) cycloaddition takes place with furan-tethered substrates, yielding densely functionalised 5,7-fused heterocycles related to the bioactive curcusone natural products. Indole-tethered substrates display divergent reactivity giving biologically important tetrahydro-β-carbolines via a Friedel-Crafts mechanism.

Highly active phosphite gold(i) catalysts for intramolecular hydroalkoxylation, enyne cyclization and furanyne cyclization

New and highly active mononuclear phosphite gold(i) catalysts are described. Turn-over numbers up to 37-000 for the furan-yne reaction and up to 28-000-000 for the two-fold hydroalkoxylation of alkynes are reported.

Combining gold and palladium catalysis: One-pot access to pentasubstituted arenes from furan-yne and En-diyne substrates

A series of furan-yne systems was transformed into the corresponding tetrasubstituted annelated phenol derivatives that bear one bromo group. The two-step procedure consisted of a phenol synthesis and a subsequent electrophilic bromination with N-bromosuccinimide (NBS). The reactions can be performed in a one-pot procedure with the same precatalyst. The halogenation reaction is highly selective only in the presence of the gold catalyst. En-diyne substrates were also suitable starting materials; then the pentasubstituted aromatic core showed a completely different substitution pattern for the phenolic products. Furthermore, a one-pot protocol that consisted of a gold-catalyzed phenol synthesis, a gold-catalyzed halogenation reaction, and a palladium-catalyzed Suzuki coupling was established. The overall efficiency of this procedure was excellent and the substrate scope of the reaction was broad. Copyright

High chemoselectivity in the phenol synthesis

Efforts to trap early intermediates of the gold-catalyzed phenol synthesis failed. Neither inter- nor intramolecularly offered vinyl groups, ketones or alcohols were able to intercept the gold carbenoid species. This indicates that the competing steps of

Gold catalysis: Phenol synthesis in the presence of functional groups

The effect of different substituants, such as bromo, chloromethyl, hydroxymethyl, formyl, acetyl, carboxy, and acylated hydroxymethyl and ammonium groups, on the furan ring of substrates in gold-catalyzed phenol synthesis has been investigated. The furan