30858-18-5

Upstream product

• 6165-68-0 thiophene boronic acid 
• 56671-81-9 3-bromo-2-cyclohexen-1-one 
• 6193-47-1 cyclopropyl(2-thienyl)methanone 
• 201230-82-2 carbon monoxide 
• 15475-25-9 2‐(1‐cyclopropylvinyl)thiophene 
• 88-15-3 2-Acetylthiophene 
• 598-32-3 2-hydroxy-3-butene 
• 188290-36-0 thiophene 
• 930-68-7 cyclohexenone 
• 15321-51-4 diiron nonacarbonyl 
• 5323-87-5 3-Ethoxycyclohex-2-en-1-one 
• 5713-61-1 thiophen-2-yl magnesium bromide 
• 504-02-9 1,3-cylohexanedione 
• 56671-82-0 3-Iodocyclohex-2-enone 

Downstream Products

• 1613527-49-3 C₁₂H₁₃NOS 
• 29886-66-6 2-(3'-hydroxyphenyl)thiophene 
• 1312208-27-7 (S)-3-(nitromethyl)-3-(thiophen-2-yl)cyclohexanone 

Relevant academic research and scientific papers

Palladium-Catalyzed Controllable Reductive/Oxidative Heck Coupling between Cyclic Enones and Thiophenes via C-H Activation

Herein, we report a straightforward, environmentally friendly, and controllable palladium/ligand catalytic system to enable reductive/oxidative Heck reactions of cyclic enones with thiophene or furan derivatives via C-H activation. The key to this tunable reaction is the appropriate intercepting thienyl-Pd(II)-enolate during the enolization process. Such a controllable and economic protocol would not only provide efficient methods to construct various value-added β-heteroarylated cyclic ketones/enones but also shed light on developing other conjugate addition reactions via C-H activation.

Palladium mediated one-pot synthesis of 3-aryl-cyclohexenones and 1,5-diketones from allyl alcohols and aryl ketones

One-pot synthesis of Robinson annulated 3-aryl-cyclohexenones from allyl alcohols and ketones using palladium is reported. Long chain aliphatic or aryl substitutions at the C1 position of allyl alcohol result in the formation of 1,5-diketone products. This simple one-pot method avoids the use of highly electrophilic vinyl ketones.

Palladium-catalyzed dehydrogenative coupling of cyclic enones with thiophenes: A rapid access to β-heteroarylated cyclic enones

Dehydrogenative coupling of cyclic enones with heteroarenes has been a longstanding challenge because of the competitive ketone dehydrogenation and conjugated addition. Herein, a dehydrogenative coupling reaction of cyclic enones of different sizes with substituted thiophenes to construct β-thienyl cyclic enone compounds through palladium-catalyzed C-H functionalization under mild reaction conditions is reported. Simple substituted thiophenes with different functional groups can be directly introduced into cyclic enones with predominant regioselectivity at the α position of thiophene moieties and excellent functional group tolerance. Further molecular transformations of the coupling products to synthetically useful meta-heteroarylated phenol derivatives have also been demonstrated.

An Electrophilic Trifluoromethylthiolation of Silylenol Ethers and β-Naphthols with Diethylaminosulfur Trifluoride and (Trifluoromethyl)trimethylsilane

An efficient and general trifluoromethylthiolation of silylenol ethers and β-naphthols have been accomplished employing the combination of diethylaminosulfur trifluoride (DAST) and (trifluoromethyl)trimethylsilane (CF3TMS) as source of electrophilic trifluoromethylthio moiety for the synthesis of α-trifluoromethylthiolated carbonyl compounds and β-naphthols in good yields. Important features of this method include wide functional group tolerance and use of readily available DAST/CF3TMS. Potential of the methodology was demonstrated via the synthesis of α-trifluoromethylthiolated (+)-4-cholesten-3-one and naphthoquinone. (Figure presented.).

Fe2(CO)9-mediated [5+1] cycloaddition of vinylcyclopropanes and CO for the synthesis of α, β-cyclohexenones

A Fe2(CO)9-mediated [5+1] cycloaddition of vinylcyclopropanes (VCPs) and CO to α, β-cyclohexenones has been developed. The reaction can tolerate aryl and aliphatic groups at the α-position of VCPs, while VCP substrates with vinyl or alkynyl substitutions are not suitable ones. In addition, this reaction can also be used to synthesize bicyclic rings if an aryl group is attached to the vinyl moiety of the substrate. Compared to the Fe(CO)5-mediated [5+1] reaction, the use of cheap and safe Fe2(CO)9 and abandoning the photo-irradiation conditions are the two major advantages of the present method.

A highly efficient metal-free approach to: Meta - And multiple-substituted phenols via a simple oxidation of cyclohexenones

A novel and efficient metal-free approach to substituted phenols has been disclosed from simple and readily available cyclohexenones and cyclohexenone equivalents. Dimethyl sulfoxide (DMSO), a simple and common organic reagent, was employed as a mild oxidant in this I2-catalysis, which significantly tolerates various substituents including some easily oxidizable or reducible functionalities. The challenging meta- and multiple-substituted phenols could be well prepared by this method. The metal-free and mild oxidation make this protocol very simple, practical, and easy to handle.

Highly enantioselective synthesis of chiral cyclic allylic amines via RH-catalyzed asymmetric hydrogenation

Highly regioselective and enantioselective asymmetric hydrogenation of cyclic dienamides catalyzed by an Rh-DuanPhos complex has been developed, which provides a readily accessible method for the synthesis of chiral cyclic allylic amines in excellent enantioselectivities (up to 99% ee). The products are valuable chiral building blocks and could be easily transformed to multisubstituted cyclohexane derivatives.

Rh(I)-catalyzed [5 + 1] cycloaddition of vinylcyclopropanes and CO for the synthesis of α,β- and β,γ-cyclohexenones

A cationic Rh(I)-catalyzed [5 + 1] cycloaddition of vinylcyclopropanes and CO has been developed, affording either β,γ-cyclohexenones as major products or α,β-cyclohexenones exclusively, under different reaction conditions.

Methods and Compositions to Inhibit Edema Factor and Adenylyl Cyclase

Small molecules and their derivatives are described for the treatment and/or prevention of intestinal fluid loss. Also disclosed are methods of using said molecules and their derivatives to treat and/or prevent conditions associated with increased levels