33414-83-4

Upstream product

• 1483-82-5 phenylethynyl chloride 
• 542-18-7 cyclohexyl chloride 
• 25411-73-8 diethyl diazomethylphosphonate 
• 712-50-5 Cyclohexyl phenyl ketone 
• 932-88-7 1-iodo-2-phenylethyne 
• 24371-94-6 cyclohexylmercury chloride 
• 35460-31-2 (2-phenylsulfanylethynyl)benzene 
• 144363-68-8 1-nitro-1-<(E)-styryl>cyclohexane 
• 110-82-7 cyclohexane 
• 52843-77-3 phenylethynyl trifluoromethyl sulfone 
• 626-62-0 Cyclohexyl iodide 
• 932-87-6 1-Bromo-2-phenylacetylene 
• 108-86-1 bromobenzene 
• 931-48-6 2-cyclohexylacetylene 

Downstream Products

• 5452-52-8 2-cyclohexylidene-1-phenyl-1-ethanone 
• 1268468-15-0 C₁₅H₁₈O₂ 
• 1283231-62-8 (Z)-2-(1-cyclohexyl-2-phenylvinyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1610681-67-8 1-(3-cyclohexyl-2-phenylindol-1-yl)ethanone 
• 1610681-68-9 1-(2-cyclohexyl-3-phenylindol-1-yl)ethanone 

Relevant academic research and scientific papers

Iodine-Zinc Exchange Reactions Mediated by i-Pr2Zn. A New Preparation of Secondary Zinc Reagents

By treatment with i-Pr2Zn, functionalized secondary alkyl iodides undergo a smooth iodine-zinc exchange reaction leading to polyfunctional secondary dialkylzinc derivatives. Remarkably, i-Pr2Zn generated in situ from i-PrMgBr and ZnBr2 undergoes this exchange reaction almost 200 times faster than salt free i-Pr2Zn and constitutes a practical source of i-Pr2Zn for the performance of exchange reactions.

Photoredox catalyzed C(sp3)[sbnd]C(sp) coupling of dihydropyridines and alkynylbenziodoxolones

A visible light mediated deformylative alkynylation of aldehydes is presented. Under photo irradiation, 1,4-dihydropyridine (DHP), derived from an aldehyde, generated a C(sp3)- radical which couples with an alkynylbenziodoxolone to generate an

Boryl Radical-Mediated C?H Activation of Inactivated Alkanes for the Synthesis of Internal Alkynes

An intriguing pyridine-boryl radical-mediated C?H alkynylation reaction of inactivated alkanes was described. The reaction features mild operation condition and wide substrate scope, and affords the corresponding products in moderate to good yields. Notab

Direct Photoexcitation of Ethynylbenziodoxolones: An Alternative to Photocatalysis for Alkynylation Reactions**

Ethynylbenziodoxolones (EBXs) are commonly used as radical traps in photocatalytic alkynylations. Herein, we report that aryl-substituted EBX reagents can be directly activated by visible light irradiation. They act as both oxidants and radical traps, alleviating the need for a photocatalyst in several reported EBX-mediated processes, including decarboxylative and deboronative alkynylations, the oxyalkynylation of enamides and the C?H alkynylation of THF. Furthermore, the method could be applied to the synthesis of alkynylated quaternary centers from tertiary alcohols via stable oxalate salts and from tertiary amines via aryl imines. A photocatalytic process using 4CzIPN as an organic dye was also developed for the deoxyalkynylation of oxalates.

Decarbonylative Sonogashira Cross-Coupling of Carboxylic Acids

Decarbonylative Sonogashira cross-coupling of carboxylic acids by palladium catalysis is presented. The carboxylic acid is activated in situ by the formation of a mixed anhydride and further decarbonylates using the Pd(OAc)2/Xantphos system to provide an aryl-Pd intermediate, which is intercepted by alkynes to access the traditional Pd(0)/(II) cycle using carboxylic acids as ubiquitous and orthogonal electrophilic cross-coupling partners. The methodology efficiently constructs new C(sp2)-C(sp) bonds and can be applied to the derivatization of pharmaceuticals. Mechanistic studies give support to decarbonylation preceding transmetalation in this process.

Nickel-Catalyzed Sonogashira Coupling Reactions of Nonactivated Alkyl Chlorides under Mild Conditions

The two nickel chlorides1and2with [P,S] and [P,Se] bidentate ligands, respectively, were synthesized and used as catalysts for Sonogashira coupling reaction. Both1and2are efficient catalysts for Sonogashira C(sp3)-C(sp) coupling reactions. Comp

Phosphine Evaluation on a New Series of Heteroleptic Copper(I) Photocatalysts with dpa Ligand [Cu(dpa)(P,P)]BF4

Five new heteroleptic copper(I) complexes (C1-5) of the type [Cu(dpa)(P,P)]BF4 based on dipyridylamine (dpa) as N,N ligand and commercial diphosphines as P,P ancillary ligands have been synthesised through a simple methodology with high yields. All complexes were thoroughly characterised by spectroscopic and spectrometric techniques, as well by theoretical calculations. These showed Metal to Ligand Charge Transfer (MLCT) absorptions in the 300–370 nm region, and emission in the 450–520 nm region with quantum yields and lifetimes that depend on the nature of the P,P ligand. The photocatalytic performance of copper(I) complexes C1-5 was evaluated for their use as photoredox catalysts in ATRA reactions, decarboxylative coupling and an Appel-type reaction. The use of readily available dpa as N,N ligand constitutes an attractive alternative to the well-established phenanthroline ligands typically used in photocatalysis.

1- And 2-Azetines via Visible Light-Mediated [2 + 2]-Cycloadditions of Alkynes and Oximes

Azetines, four-membered unsaturated nitrogen-containing heterocycles, hold great potential for drug design and development but remain underexplored due to challenges associated with their synthesis. We report an efficient, visible light-mediated approach

Ligand-free (: Z)-selective transfer semihydrogenation of alkynes catalyzed by in situ generated oxidizable copper nanoparticles

Herein, we present (Z)-selective transfer semihydrogenation of alkynes based on in situ generated CuNPs in the presence of hydrogen donors, such as ammonia-borane and a green protic solvent. This environmentally friendly method is characterized by operational simplicity combined with high stereo- and chemoselectivity and functional group compatibility. Auto-oxidation of CuNPs after the completion of a semihydrogenation reaction results in the formation of a water-soluble ammonia complex, so that the catalyst may be reused several times by simple phase-separation with no need for any special regeneration processes. Formed NH4B(OR)4 can be easily transformed back into ammonia-borane or into boric acid. In addition, a one-pot tandem sequence involving a Suzuki reaction followed by semihydrogenation was presented, which allows minimization of chemical waste production.

Photoinduced Palladium-Catalyzed Dicarbofunctionalization of Terminal Alkynes

Herein, a conceptually distinct approach was developed that allowed for the dicarbofunctionalization of alkynes at room temperature using simple, bench-stable alkyl iodides and a second molecule of alkyne as coupling partner. Specifically, the photochemical activation of palladium complexes enabled this strategic dicarbofunctionalization via addition of alkyl radicals from secondary and tertiary alkyl iodides and formation of an intermediate palladium vinyl complex that could undergo subsequent Sonogashira reaction with a second alkyne molecule. This alkylation–alkynylation sequence allowed the one-step synthesis of 1,3-enynes including heteroarenes and biologically active compounds with high efficiency without exogenous photosensitizers or oxidants and now opens up pathways towards cascade reactions via photochemical palladium catalysis.