59824-24-7

Upstream product

• 22966-17-2 4-cyanochalcone 
• 3435-51-6 4-ethenylbenzonitrile 
• 93-97-0 benzoic acid anhydride 
• 98-86-2 acetophenone 
• 105-07-7 4-cyanobenzaldehyde 
• 100-52-7 benzaldehyde 
• 98-85-1 1-Phenylethanol 
• 874-89-5 4-Cyanobenzyl alcohol 
• 72758-75-9 (E)-4-(3-oxo-3-phenylprop-1-en-1-yl)benzonitrile 

Downstream Products

• 1446018-12-7 4-((2-(4-methoxybenzylamino)-4-phenylthiazol-5-yl)methyl)benzonitrile 
• 70802-89-0 1-Phenyl-2-brom-3-(4-cyanphenyl)-propanon-1 
• 1621006-64-1 4-((2-amino-4-phenylthiazol-5-yl)methyl)benzonitrile 

Relevant academic research and scientific papers

Borane-Catalyzed, Chemoselective Reduction and Hydrofunctionalization of Enones Enabled by B-O Transborylation

The use of stoichiometric organoborane reductants in organic synthesis is well established. Here these reagents have been rendered catalytic through an isodesmic B-O/B-H transborylation applied in the borane-catalyzed, chemoselective alkene reduction and formal hydrofunctionalization of enones. The reaction was found to proceed by a 1,4-hydroboration of the enone and B-O/B-H transborylation with HBpin, enabling catalyst turnover. Single-turnover and isotopic labeling experiments supported the proposed mechanism of catalysis with 1,4-hydroboration and B-O/B-H transborylation as key steps.

Neutral-eosin Y-catalyzed regioselective hydroacylation of aryl alkenes under visible-light irradiation

Styrene derivatives were hydroacylated with exclusive anti-Markovnikov selectivity by using neutral eosin Y as a direct hydrogen-atom-transfer (HAT) catalyst under visible-light irradiation. Aldehydes and styrenes with various substituents were tolerated (>20 examples), giving the corresponding products in moderate to high yields. The key acyl radical intermediate was generated from a direct HAT process induced by photoexcited eosin Y. Subsequent addition to styrenes and a reverse HAT process generated the ketone products.

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.

Nickel-Catalyzed Alkylation of Ketone Enolates: Synthesis of Monoselective Linear Ketones

Herein we have developed a Ni-catalyzed protocol for the synthesis of linear ketones. Aryl, alkyl, and heteroaryl ketones as well as alcohols yielded the monoselective ketones in up to 90% yield. The catalytic protocol was successfully applied in to a gram-scale synthesis. For a practical utility, applications of a steroid derivative, oleyl alcohol, and naproxen alcohol were employed. Preliminary catalytic investigations involving the isolation of a Ni intermediate and defined Ni-H species as well as a series of deuterium-labeling experiments were performed.

Manganese-Catalyzed α-Alkylation of Ketones, Esters, and Amides Using Alcohols

Herein we report the manganese-catalyzed C-C bond-forming reactions via α-alkylation of ketones, amides, and esters, using primary alcohols. β-Alkylation of secondary alcohols by primary alcohols to obtain α-alkylated ketones is also reported. The reactions are catalyzed by a (iPr-PNP)Mn(H)(CO)2 pincer complex under mild conditions in the presence of (catalytic) base liberating water (and H2 in the case of secondary alcohol alkylation) as the sole byproduct.

Transition-Metal-Free Synthesis of Homo- and Hetero-1,2,4-Triaryl Benzenes by an Unexpected Base-Promoted Dearylative Pathway

An unprecedented approach for the synthesis of homo- and hetero-1,2,4-triaryl benzenes has been developed using a simple base-mediated reaction of either α-aryl cinnamyl alcohols or α,γ-di-aryl propanones. The salient feature of this strategy involves the sequential hydride transfer, regiospecific condensation, regiospecific dearylation, and aromatization under metal-free reaction conditions. The synthesis of unsymmetrically substituted triphenylenes by oxidative coupling of the synthesized 1,2,4-triaryl benzenes has also been demonstrated.

2,4,5-Trisubstituted thiazole derivatives: A novel and potent class of non-nucleoside inhibitors of wild type and mutant HIV-1 reverse transcriptase

Novel 2,4,5-trisubstituted thiazole derivatives (TSTs) were designed and synthesized as HIV-1 non-nucleoside reverse transcriptase inhibitors (NNRTIs). Among the thirty-eight synthesized target compounds, thirty TSTs showed potent inhibition against HIV-1 replication in wild type HIV-1 at submicromolar concentrations (from 0.046 to 9.59 μM). Compounds 21, 23 and 24 were also tested on seven NNRTI-resistant HIV-1 strains, and all exhibited inhibitory effects with fold changes in IC50 ranging from 2.6 to 111, which were better than those of nevirapine (15.6-fold-371-fold). Docking simulations of compound 24 revealed a reasonable mechanism for the binding mode, and three-dimensional quantitative structure activity relationship (3-DQSAR) studies on this novel series of TST further elucidated the structure-activity relationship (SAR). The results suggested the great potential of TSTs as a novel class of NNRTIs with antiviral efficacy and a good resistance profile.

NHC-catalyzed hydroacylation of styrenes

New hydroacylation catalysts: Highly electron-rich N-heterocyclic carbenes (NHCs) facilitate the intermolecular hydroacylation of unstrained olefins. This unprecedented organocatalytic coupling joins simple and abundant aldehydes and styrenes to yield valuable ketone products. EWG=electron-withdrawing group, EDG=electron-donating group. Copyright

Branch-selective intermolecular hydroacylation: Hydrogen-mediated coupling of anhydrides to styrenes and activated olefins

(Chemical Equation Presented) Branching out with hydrogen: Hydrogenation of symmetric or mixed carboxylic anhydrides in the presence of styrenes or activated olefins generates intermolecular hydroacylation products. The use of cationic rhodium catalysts ligated by triphenylarsine (Ph3As) results in the formation of branched coupling products as single regioisomers in high yields (see scheme; cod = cycloocta-1,5-diene, ArF = 3,5-(CF 3)2C6H3).