40027-94-9

Upstream product

• 188290-36-0 thiophene 
• 645-45-4 hydrocinnamic acid chloride 
• 102-92-1 cinnamoyl chloride 
• 5713-61-1 thiophen-2-yl magnesium bromide 
• 645-59-0 dihydrocinnamonitrile 
• 501-52-0 3-Phenylpropionic acid 
• 88-15-3 2-Acetylthiophene 
• 100-51-6 benzyl alcohol 
• 100-52-7 benzaldehyde 
• 2786-07-4 2-thienyl lithium 
• 3988-77-0 3-phenyl-1-thiophen-2-yl-propenone 
• 3988-77-0 2-cinnamoylthiophene 
• 458-69-5 3-phenylpropanoic acid fluoride 
• 133745-75-2 N-fluorobis(benzenesulfon)imide 

Downstream Products

• 108664-49-9 1-(2-thienyl)-2-benzyl-2-propen-1-one 
• 737729-36-1 3,3-Dimethyl-5-[5-(3-phenyl-propyl)-thiophen-2-yl]-pentylamine 
• 1026376-87-3 3,3-Dimethyl-5-[5-(3-phenyl-propyl)-thiophen-2-yl]-1-[4-(2,3,4-trimethoxy-benzyl)-piperazin-1-yl]-pentan-1-one 
• 1026433-71-5 1-Morpholin-4-yl-2-(1-{2-[5-(3-phenyl-propyl)-thiophen-2-yl]-ethyl}-cyclopentyl)-ethanone 
• 1027901-11-6 3-Methyl-1-morpholin-4-yl-5-[5-(3-phenyl-propyl)-thiophen-2-yl]-pentan-1-one 
• 136573-27-8 3,3-Dimethyl-1-morpholin-4-yl-5-[5-(3-phenyl-propyl)-thiophen-2-yl]-pentan-1-one 
• 1026170-72-8 1-Morpholin-4-yl-5-[5-(3-phenyl-propyl)-thiophen-2-yl]-pentan-1-one 
• 214618-38-9 (1-{2-[5-(3-Phenyl-propyl)-thiophen-2-yl]-ethyl}-cyclopentyl)-acetic acid 

Relevant academic research and scientific papers

Cobalt-catalyzed Divergent Markovnikov and Anti-Markovnikov Hydroamination

Catalytic hydroamination of the readily available alkenes is among the most straightforward means to construct diverse alkyl amines. To this end, the facile access to both regioselectivity, i.e., Markovnikov or anti-Markovnikov hydroamination, with minimum reaction-parameter alternation, remains challenging. Herein, we report a cobalt-catalyzed highly selective and divergent Markovnikov and anti-Markovnikov hydroamination of alkenes, in which the switch of regioselectivity is achieved simply by the variation of the addition sequence of 9-BBN.

Selective catalytic synthesis of α-alkylated ketones and β-disubstituted ketones via acceptorless dehydrogenative cross-coupling of alcohols

Herein, a phosphine-free pincer ruthenium(III) catalyzed β-alkylation of secondary alcohols with primary alcohols to α-alkylated ketones and two different secondary alcohols to β-branched ketones are reported. Notably, this transformation is environmentally benign and atom efficient with H2O and H2 gas as the only byproducts. The protocol is extended to gram-scale reaction and for functionalization of complex vitamin E and cholesterol derivatives.

Direct conversion of secondary propargyl alcohols into 1,3-di-arylpropanoneviaDBU promoted redox isomerization and palladium assisted chemoselective hydrogenation in a single pot operation

Palladium(ii)acetate is found to be an efficient catalyst for the single-step conversion of secondary propargyl alcohols to 1,3-diarylpropanone derivatives under mild basic conditions. The reaction is believed to proceedviaredox isomerisation of secondary propargyl alcohols followed by chemoselective reduction of an enone double bond with formic acid as an adequate hydrogen donor. A large number of 1,3-diarylpropanone derivatives may readily be prepared from a milligram to a multigram scale.

Visible-Light Decatungstate/Disulfide Dual Catalysis for the Hydro-Functionalization of Styrenes

We describe an efficient photoredox system, relying on decatungstate/disulfide catalysts, for the hydrofunctionalization of styrenes. In this methodology the use of disulfide as a cocatalyst was shown to be crucial for the reaction efficiency. This photoredox system was employed for the hydro-carbamoylation, -acylation, -alkylation, and -silylation of styrenes, giving access to a large variety of useful building blocks and high-value molecules such as amides and unsymmetrical ketones from simple starting materials.

Iron-catalyzed chemoselective hydride transfer reactions

A Diaminocyclopentadienone iron tricarbonyl complex has been applied in chemoselective hydrogen transfer reductions. This bifunctional iron complex demonstrated a broad applicability in mild conditions in various reactions, such as reduction of aldehydes over ketones, reductive alkylation of various functionalized amines with functionalized aldehydes and reduction of α,β-unsaturated ketones into the corresponding saturated ketones. A broad range of functionalized substrates has been isolated in excellent yields with this practical procedure.

Efficient cleavage of tertiary amide bonds: Via radical-polar crossover using a copper(ii) bromide/Selectfluor hybrid system

A novel approach for the efficient cleavage of the amide bonds in tertiary amides is reported. Based on the selective radical abstraction of a benzylic hydrogen atom by a CuBr2/Selectfluor hybrid system followed by a selective cleavage of an N-C bond, an acyl fluoride intermediate is formed. This intermediate may then be derivatized in a one-pot fashion. The reaction proceeds under mild conditions and exhibits a broad substrate scope with respect to the tertiary amide moiety as well as to nitrogen, oxygen, and carbon nucleophiles for the subsequent derivatization. Mechanistic studies suggest that the present reaction proceeds via a radical-polar crossover process that involves benzylic carbon radicals generated by the selective radical abstraction of a benzylic hydrogen atom by the CuBr2/Selectfluor hybrid system. Furthermore, a synthetic application of this method for the selective cleavage of peptides is described. This journal is

Sustainable and Selective Alkylation of Deactivated Secondary Alcohols to Ketones by Non-bifunctional Pincer N-heterocyclic Carbene Manganese

A sustainable and green route to access diverse functionalized ketones via dehydrogenative–dehydrative cross-coupling of primary and secondary alcohols is demonstrated. This borrowing hydrogen approach employing a pincer N-heterocyclic carbene Mn complex displays high activity and selectivity. A variety of primary and secondary alcohols are well tolerant and result in satisfactory isolated yields. Mechanistic studies suggest that this reaction proceeds via a direct outer-sphere mechanism and the dehydrogenation of the secondary alcohol substrates plays a vital role in the rate-limiting step.

Visible-Light-Promoted Photocatalyst-Free Hydroacylation and Diacylation of Alkenes Tuned by NiCl2·DME

Herein, we describe a visible light-promoted hydroacylation strategy that facilitates the preparation of ketones from alkenes and 4-acyl-1,4-dihydropyridines via an acyl radical addition and hydrogen atom transfer pathway under photocatalyst-free conditions. The efficiency was highlighted by wide substrate scope, good to high yields, successful scale-up experiments, and expedient preparation of highly functionalized ketone derivatives. In addition, this protocol allows for the synthesis of 1,4-dicarbonyl compounds through alkene diacylation in the presence of NiCl2·DME.

Chemoselective Hydrosilylation of the α,β-Site Double Bond in α,β- And α,β,γ,δ-Unsaturated Ketones Catalyzed by Macrosteric Borane Promoted by Hexafluoro-2-propanol

The B(C6F5)3-catalyzed chemoselective hydrosilylation of α,β- and α,β,γ,δ-unsaturated ketones into the corresponding non-symmetric ketones in mild reaction conditions is developed. Nearly 55 substrates including those bearing reducible functional groups such as alkynyl, alkenyl, cyano, and aromatic heterocycles are chemoselectively hydrosilylated in good to excellent yields. Isotope-labeling studies revealed that hexafluoro-2-propanol also served as a hydrogen source in the process.

Reaction condition controlled nickel(ii)-catalyzed C-C cross-coupling of alcohols

The challenge in the C-C cross-coupling of secondary and primary alcohols using acceptorless dehydrogenation coupling (ADC) is the difficulty in accurately controlling product selectivities. Herein, we report a controlled approach to a diverse range of β-alkylated secondary alcohols, α-alkylated ketones and α,β-unsaturated ketones using the ADC methodology employing a Ni(ii) 4,6-dimethylpyrimidine-2-thiolate cluster catalyst under different reaction conditions. This catalyst could tolerate a wide range of substrates and exhibited a high activity for the annulation reaction of secondary alcohols with 2-aminobenzyl alcohols to yield quinolines. This work is an example of precise chemoselectivity control by careful choice of reaction conditions.