35776-38-6

Upstream product

• 2398-37-0 3-methoxyphenyl bromide 
• 766-85-8 3-methoxy-1-iodobenzene 
• 100-66-3 methoxybenzene 
• 870485-34-0 (3-methoxyphenyl)(triphenyl-λ5-phosphanyl)gold 
• 586-38-9 3-Methoxybenzoic acid 

Downstream Products

• 696-62-8 para-iodoanisole 

Relevant academic research and scientific papers

Copper-Catalyzed Cycloaddition of Heterobicyclic Alkenes with Diaryl Disulfides to Synthesize Dihydrobenzo[b]thiophene Derivatives

A novel copper-catalyzed cycloaddition of diaryl disulfides to heterobicyclic alkenes has been developed. The C - S and C - C bonds can be formed simultaneously on the C═C bond of the olefins via a single-step cycloaddition to afford a series of 2,3-dihydrobenzo[b]thiophene derivatives. This reaction exhibits excellent diastereoselectivity and relatively broad substrate scope. Various functional groups attached to the substrates are tolerated in this protocol to give the corresponding exo adducts in moderate yields.

Copper-catalysed low-temperature water-gas shift reaction for selective deuteration of aryl halides

The introduction of deuterium atoms into organic compounds is of importance for basic chemistry, material sciences, and the development of drugs in the pharmaceutical industry, specifically for identification and quantification of metabolites. Hence, methodologies for the synthesis of selectively labelled compounds continue to be a major area of interest for many scientists. Herein, we present a practical and stable heterogeneous copper catalyst, which permits for dehalogenative deuterationviawater-gas shift reaction at comparably low temperature. This novel approach allows deuteration of diverse (hetero)aryl halides with good functional group tolerance, and no reduction of the aromatic rings or other easily reducible formyl and cyano groups. Multi-gram experiments show the potential of this method in organic synthesis and medicinal chemistry.

Electrocatalytic Deuteration of Halides with D2O as the Deuterium Source over a Copper Nanowire Arrays Cathode

Precise deuterium incorporation with controllable deuterated sites is extremely desirable. Here, a facile and efficient electrocatalytic deuterodehalogenation of halides using D2O as the deuteration reagent and copper nanowire arrays (Cu NWAs) electrochemically formed in situ as the cathode was demonstrated. A cross-coupling of carbon and deuterium free radicals might be involved for this ipso-selective deuteration. This method exhibited excellent chemoselectivity and high compatibility with the easily reducible functional groups (C=C, C≡C, C=O, C=N, C≡N). The C?H to C?D transformations were achieved with high yields and deuterium ratios through a one-pot halogenation–deuterodehalogenation process. Efficient deuteration of less-active bromide substrates, specific deuterium incorporation into top-selling pharmaceuticals, and oxidant-free paired anodic synthesis of high-value chemicals with low energy input highlighted the potential practicality.

Visible-Light-Photosensitized Aryl and Alkyl Decarboxylative Functionalization Reactions

Despite significant progress in aliphatic decarboxylation, an efficient and general protocol for radical aromatic decarboxylation has lagged far behind. Herein, we describe a general strategy for rapid access to both aryl and alkyl radicals by photosensitized decarboxylation of the corresponding carboxylic acids esters followed by their successive use in divergent carbon–heteroatom and carbon–carbon bond-forming reactions. Identification of a suitable activator for carboxylic acids is the key to bypass a competing single-electron-transfer mechanism and “switch on” an energy-transfer-mediated homolysis of unsymmetrical σ-bonds for a concerted fragmentation/decarboxylation process.

Cobalt-catalyzed annulation of aryl iodides with alkynes

A cobalt-catalyzed approach for the concise synthesis of naphthalenes by the annulation of aryl iodides with alkynes is disclosed. In the reaction, manganese reductant and MeCN solvent are necessary to proceed efficiently, which tolerates various functional groups, for example, boronate ester. Mechanistic investigation indicates that the transformation employs electrophilic aromatic substitution (SEAr) in the aromatic C-H bond replacement step.

Gold-catalysis: Reactions of organogold compounds with electrophiles

Different arylgold(I), one alkynylgold(I), and one vinylgold(I) triphenylphosphane complexes were subjected to electrophilic halogenation reagents. With N-chlorosuccinimid, N-bromosuccinimid, and N-iodosuccinimid as well as the Barluenga reagent, selectively halogenated compounds were obtained. Trifluoroacetic acid, as a source of protons, leads to a clean protodeauration. With N-fluorobenzenesulfonimide or Selectfluor, exclusively a homocoupling was observed. For the precursor of the vinylgold(I) complex, a similar oxidative coupling could be induced by gold(III) chloride. Reactions with silicon or tin electrophiles failed. CSIRO 2010.

Synthesis, structure and reactivity of organogold compounds of relevance to homogeneous gold catalysis

Organogold(I) phosphane complexes were prepared, their structure was investigated and their reactivity in reactions with Michael acceptors, sources of electrophilic halogens and protons were investigated.