165557-64-2

Upstream product

• 619-58-9 4-iodobenzoic acid 
• 2216-51-5 (-)-menthol 
• 1711-02-0 4-iodobenzoic acid chloride 

Downstream Products

• 1270099-90-5 1-{[(1R,2S,5R)-(-)-menthoxycarbonyl]phenyl}-2-phenylacetylene 
• 169968-84-7 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 4-hydroxybenzoate 

Relevant academic research and scientific papers

Photocatalyst-Free Visible-Light-Promoted C(sp2)-S Coupling: A Strategy for the Preparation of S-Aryl Dithiocarbamates

We have successfully developed a green and efficient multicomponent reaction protocol to synthesize S-aryl dithiocarbamates under visible light. Most appealingly, the reaction can proceed smoothly without adding any transition-metal catalysts, ligands, or photocatalysts while minimizing chemical wastes and metal residues in the end products. The advantages of this method meet the requirements of sustainable and green synthetic chemistry, and it provides a straightforward way to create valuable S-aryl dithiocarbamates.

Sulfonylation of Aryl Halides by Visible Light/Copper Catalysis

An efficient visible-light-assisted, copper-catalyzed sulfonylation of aryl halides with sulfinates is reported. In our protocol, a single ligand CuI photocatalyst formed in situ was used in the photocatalytic transformation. Diverse organosulfones were obtained in moderate to good yields. This strategy demonstrates a promising approach toward the synthesis of diverse and useful organosulfones.

Engaging 1,7-diynes in a photocatalytic Kharasch-type addition/1,5-(SN′′)-substitution cascade toward β-gem-dihalovinyl carbonyls

A new and general photocatalytic Kharasch-type addition/1,5-(SN′′)-substitution cascade of 1,7-diynes with alkyl halides such as BrCCl3and CBr4was reported for the first time, and used to produce 65 hitherto unreported β-gem-dihalovinyl ketones/aldehydes with moderate to excellent yields in a highly regioselective manner. This reaction tolerates a wide scope of substrates, which offers a green and efficient entry to fabricate synthetically important β-gem-dihalovinyl carbonyl scaffolds. Notably, the late-stage application of these resulting β-gem-dihalovinyl carbonyls shows high and unique reactivity profiles and demonstrates the versatility of their derivatization.

Highly efficient heterogeneous V2O5@TiO2 catalyzed the rapid transformation of boronic acids to phenols

A V2O5@TiO2 catalyzed green and efficient protocol for the hydroxylation of boronic acid into phenol has been developed utilizing environmentally benign oxidant hydrogen peroxide. A wide range of electron-donating and the electron-withdrawing group-containing (hetero)aryl boronic acids were transformed into their corresponding phenol. The methodology was also applied successfully to transform various natural and bioactive molecules like tocopherol, amino acids, cinchonidine, vasicinone, menthol, and pharmaceuticals such as ciprofloxacin, ibuprofen, and paracetamol. The other feature of the methodology includes gram-scale synthetic applicability, recyclability, and short reaction time.

Copper-catalyzed and additive free decarboxylative trifluoromethylation of aromatic and heteroaromatic iodides

A copper-catalyzed decarboxylative trifluoromethylation of (hetero)aromatic iodides has been developed. Importantly, this new copper-catalyzed reaction operates in the absence of any ligands and metal additives. The protocol shows good functional group tolerance and is compatible with heteroaromatic systems. The reaction proved scalable to a 15 mmol scale with increased yield. Finally, late-stage installation of the trifluoromethyl functionality afforded the N-trifluoroacetamide variant of the antidepressant agent, Prozac, demonstrating the applicability of the developed method.

Synthesis of Acyclic Aliphatic Amides with Contiguous Stereogenic Centers via Palladium-Catalyzed Enantio-, Chemo- and Diastereoselective Methylene C(sp3)?H arylation

The enantioselective desymmetrizing C?H activation of α-gem-dialkyl acyclic amides remains challenging because the availability of four chemically identical unbiased methylene C(sp3)?H bonds and increased rotational freedoms of the acyclic systems add tremendous difficulties for chemo- and stereocontrol. We have developed a method for the synthesis of acyclic aliphatic amides with α,β-contiguous stereogenic centers via PdII-catalyzed asymmetric arylation of unbiased methylene C(sp3)?H, in good yields and with high levels of enantio-, chemo- and diastereoselectivity (up to >99 % ee and >20:1 d.r.). Successive application of this method enables the sequential arylation of the gem-dialkyl groups with two different aryl iodides, giving a range of β-Ar1-β′-Ar2-aliphatic acyclic amides containing three contiguous stereogenic centers with excellent diastereoselectivity.

Photoinduced Hydroxylation of Organic Halides under Mild Conditions

Presented in this paper is photoinduced hydroxylation of organic halides, providing a mild access to a range of functionalized phenols and aliphatic alcohols. These reactions generally proceed under mild reaction conditions with no need for a photocatalyst or a strong base and show a wide substrate scope as well as excellent functional group tolerance. This work highlights the unique role of NaI that allows a challenging transformation to proceed under mild reaction conditions.

Macrocyclization of biaryl-bridged peptides through late-stage palladium-catalyzed C(sp2)-H Arylation

Macrocyclic peptides are promising scaffolds of bioactive compounds and clinical therapeutics. Herein, we develop a strategy for the macrocyclization of biaryl-bridged peptides through late-stage Pd-catalyzed C(sp2)-H arylation. This method dis

Catalytic Enantio- And Diastereoselective Cyclopropanation of 2-Azadienes for the Synthesis of Aminocyclopropanes Bearing Quaternary Carbon Stereogenic Centers

We report the catalytic enantio- and diastereoselective preparation of aminocyclopropanes by the cyclopropanation of terminal and (Z)-internal 2-azadienes with donor/acceptor carbenes derived from α-diazoesters. The resulting cyclopropanes bear quaternary carbon stereogenic centers vicinal to the amino-substituted carbon and are formed as a single diastereomer in up to 99:1 er and 97% yield with 0.5 mol % of Rh2(DOSP)4 and only 1.5 equiv of the diazo reagent. Transformations with internal azadienes afford cyclopropanes with three contiguous stereogenic centers.

Helical and luminescent disubstituted polyacetylenes: Synthesis, helicity, and light emission of poly(diphenylacetylene)s bearing chiral menthyl pendant groups

Diphenylacetylenes containing chiral menthyl groups [C6H 5C=C-C6H4OCOCH2OR* and C 6H5C=C-C6H4CO2R*, R* = (1R,2S,5R)-(-)-menthyl] are synthesized