1101205-38-2

Upstream product

• 850567-47-4 1-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrole and 1-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrole 
• 92-66-0 4-bromo-1,1'-biphenyl 
• 96-54-8 N-Methylpyrrole 
• 2051-62-9 4'-biphenyl chloride 
• 106-39-8 bromochlorobenzene 
• 98-80-6 phenylboronic acid 
• 1623-93-4 4-diphenylsulfonyl chloride 
• 1591-31-7 4-iodo-biphenyl 
• 92-52-4 biphenyl 

Relevant academic research and scientific papers

A General Copper Catalyst for Photoredox Transformations of Organic Halides

A broadly applicable copper catalyst for photoredox transformations of organic halides is reported. Upon visible light irradiation in the presence of catalytic amounts of [(DPEphos)(bcp)Cu]PF6 and an amine, a range of unactivated aryl and alkyl halides were shown to be smoothly activated through a rare Cu(I)/Cu(I)?/Cu(0) catalytic cycle. This complex efficiently catalyzes a series of radical processes, including reductions, cyclizations, and direct arylation of arenes.

Photochemical (Hetero-)Arylation of Aryl Sulfonium Salts

The construction of (hetero)biaryls, which are ubiquitous scaffolds among medical substances, functional materials, and agrochemicals, constitutes a key application of cross-coupling methods. However, these usually require multiple synthetic steps. Herein, we report a simple photoinduced and catalyst-free C-H/C-H (hetero)arylation cross-coupling through aryl thianthrenium salts, which are formed site-selectively by direct C-H functionalization. The key to this approach is the UV-light, which can disrupt the C-S bond to form thianthrene radical cations and aryl radicals.

Late-Stage Heteroarylation of Hetero(aryl)sulfonium Salts Activated by α-Amino Alkyl Radicals

We report a late-stage heteroarylation of aryl sulfonium salts through activation with α-amino alkyl radicals in a mechanistically distinct approach from previously reported halogen-atom transfer (XAT). The new mode of activation of aryl sulfonium salts p

Polysulfide Anions as Visible Light Photoredox Catalysts for Aryl Cross-Couplings

Polysulfide anions are endowed with unique redox properties, attracting considerable attentions for their applications in alkali metals-sulfur batteries. However, the employment of these anionic species in redox catalysis for small molecule synthesis remains underdeveloped due to their moderate-poor electrochemical potential in the ground state, whereas some of them are characterized by photoabsorptions in visible spectral regions. Herein, we disclose the use of polysulfide anions as visible light photoredox catalysts for aryl cross-coupling reactions. The reaction design enables single-electron reduction of aryl halides upon the photoexcitation of tetrasulfide dianions (S42-). The resulting aryl radicals are engaged in (hetero)biaryl cross-coupling, borylation, and hydrogenation in a redox catalytic regime involving S4?-/S42- and S3?-/S32- redox couples.

A general copper-based photoredox catalyst for organic synthesis: Scope, application in natural product synthesis and mechanistic insights

Organic transformations can broadly be classified into four categories including cationic, anionic, pericyclic and radical reactions. While the last category has been known for decades to provide remarkably efficient synthetic pathways, it has long been hampered by the need for toxic reagents, which considerably limited its impact on chemical synthesis. This situation has come to an end with the introduction of new concepts for the generation of radical species, photoredox catalysis – which simply relies on the use of a catalyst that can be activated upon visible light irradiation – certainly being the most efficient one. The state-of-the-art catalysts mostly rely on the use of ruthenium and iridium complexes and organic dyes, which still considerably limits their broad implementation in chemical processes: alternative readily available catalysts based on inexpensive, environmentally benign base metals are therefore strongly needed. Furthermore, expanding the toolbox of methods based on photoredox catalysis will facilitate the discovery of new light-mediated transformations. This article details the use of a simple copper complex which, upon activation with blue light, can initiate a broad range of radical reactions.

Visible-light photocatalyzed synthesis of 2-aryl N-methylpyrroles, furans and thiophenes utilizing arylsulfonyl chlorides as a coupling partner

Visible-light (Blue LED lamp: hν=425±15 nm) photocatalyzed cross-coupling reactions of arylsulfonyl chloride with N-methylpyrrole, furan, thiophene and their derivatives have been achieved in moderate to good yields at room temperature. A plausible mechan

Chromoselective Photocatalysis: Controlled Bond Activation through Light-Color Regulation of Redox Potentials

Catalysts that can be regulated in terms of activity and selectivity by external stimuli may allow the efficient multistep synthesis of complex molecules and pharmaceuticals. Herein, we report the light-color regulation of the redox potential of a photocatalyst to control the activation of chemical bonds. Light-color control of the redox power of a photocatalyst introduces a new selectivity parameter to photoredox catalysis: Instead of changing the catalyst or ligand, alteration of the color of the visible-light irradiation adjusts the selectivity in catalytic transformations. By using this principle, the selective activation of aryl–halide bonds for C?H arylation and the sequential conversion of functional groups with different reduction potentials is possible by simply applying different colors of light for excitation of the photocatalyst.

Expanding the scope of the Cu assisted Suzuki-Miyaura reaction

Recent advances in the development of the copper facilitated Suzuki-Miyaura reaction are described. Improvements include expansion of substrate scope to include aryl chlorides and polyhalo aryl boronates. It was found that use of S-Phos and X-Phos could a

Palladium-catalyzed indole, pyrrole, and furan arylation by aryl chlorides

The palladium-catalyzed direct arylation of indoles, pyrroles, and furans by aryl chlorides has been demonstrated. The method employs a palladium acetate catalyst, 2-(dicyclohexylphosphino)-biphenyl ligand, and an inorganic base. Electron-rich and electron-poor aryl chlorides as well as chloropyridine coupling partners can be used, and arylated heterocycles are obtained in moderate to good yields. Optimization of base, ligand, and solvent is required for achieving best results.

Copper-facilitated Suzuki reactions: Application to 2-heterocyclic boronates

(Chemical Equation Presented) The palladium-catalyzed Suzuki-Miyaura reaction has been utilized as one of the most powerful methods for C-C bond formation. However, Suzuki reactions of electron-deficient 2-heterocyclic coronates generally give low convers