104741-75-5

Upstream product

• 937-62-2 p-tolyl chloroformate 
• 865-48-5 sodium t-butanolate 
• 106-44-5 p-cresol 
• 24424-99-5 di-tert-butyl dicarbonate 

Downstream Products

• 106-44-5 p-cresol 
• 108-88-3 toluene 
• 195062-57-8 p-tolylboronic pinacol ester 
• 939784-08-4 C₂₈H₂₈N₂O₄ 
• 143090-18-0 tert-butyl N-(4-cyanophenyl)carbamate 
• 251098-53-0 C₁₂H₁₅BrO₃ 

Relevant academic research and scientific papers

Photo-induced thiolate catalytic activation of inert Caryl-hetero bonds for radical borylation

Substantial effort is currently being devoted to obtaining photoredox catalysts with high redox power. Yet, it remains challenging to apply the currently established methods to the activation of bonds with high bond dissociation energy and to substrates with high reduction potentials. Herein, we introduce a novel photocatalytic strategy for the activation of inert substituted arenes for aryl borylation by using thiolate as a catalyst. This catalytic system exhibits strong reducing ability and engages non-activated Caryl–F, Caryl–X, Caryl–O, Caryl–N, and Caryl–S bonds in productive radical borylation reactions, thus expanding the available aryl radical precursor scope. Despite its high reducing power, the method has a broad substrate scope and good functional-group tolerance. Spectroscopic investigations and control experiments suggest the formation of a charge-transfer complex as the key step to activate the substrates.

PROCESS FOR THE CATALYTIC DIRECTED CLEAVAGE OF AMIDE-CONTAINING COMPOUNDS

The present invention relates to a catalytic method for the conversion of amide-containing compouds by means of a build-in directing group and upon the action of a heteronucleophilic compound (in se an amine (RNH2 or RNHR') or an alcohol (ROH) or a thiol (RSH)) in the presence of a metal catalyst to respectively esters, thioesters, carbonates, thiocarbonates and to what is defined as amide-containing compounds (such as carboxamides, urea, carbamates, thiocarbamates). The present invention also relates to these amide-containing compounds having a build-in directing group (DG), as well as the use of such directing groups in the catalytic directed cleavage of N-DG amides with the use of heteronucleophiles (in se an amine (RNH2 or RNHR') or an alcohol (ROH) or thiol (RSH)).

Mixed metal MgO-ZrO2 nanoparticle-catalyzed O-tert-Boc protection of alcohols and phenols under solvent-free conditions

An environmentally benign method for O-tert-Boc protection of alcohols and phenols catalyzed by MgO-ZrO2 nanoparticles under solvent-free conditions is described. A variety of phenols, alcohols (aliphatic and aromatic) were converted to corresponding O-tert-Boc products in good to excellent yield (50-95%). The present protocol is expedient, simple, and efficient under solvent-free conditions. The MgO-ZrO2 Nps are easily prepared from inexpensive precursors, and are reusable, recyclable and chemoselective. Copyright 2012 John Wiley & Sons, Ltd. Copyright

An eco-sustainable erbium(iii)-catalyzed method for formation/cleavage of O-tert-butoxy carbonates

A new simple and effective method for the formation/cleavage of O-tert-butoxy carbonates of alcohols and phenols is proposed. Mesoporous silica-supported Er(iii) (ErIII-MCM-41) was used as an efficient and reusable solid catalyst in the solvent-free ultrasound-assisted synthesis of Boc-carbonate derivatives of a wide range of alcohols and phenols. The fast, selective deprotection of Boc-derivatives is achieved with a very low amount of Er(OTf)3 in ethanol under microwave irradiation. Therefore, the entire protection/de-protection process is very attractive, from the point of view of sustainability.

Triphenylphosphine as a novel organocatalyst for chemoselective O-tert-butoxycarbonylation of phenols

A novel organocatalytic procedure for the chemoselective O-tert-butoxycarbonylation of phenols under neutral and neat conditions is described. Georg Thieme Verlag Stuttgart.

Organocatalytic methods for chemoselective O-tert-butoxycarbonylation of phenols and their regeneration from the O-t-Boc derivatives

(Chemical Equation Presented) Carbon tetrabromide (CBr4) catalyzes O-tert-butoxycarbonylation of functionalized phenols without any side reactions (bromination, addition of CBr3 to a double bond, and formation of symmetrical diaryl carbonates, cyclic carbonates, or carbonic-carbonic anhydrides). The parent phenols are regenerated from the O-t-Boc derivatives by the catalyst system CBr4-PPh3 without affecting other protecting groups (aryl alkyl ether, alkyl ester, and thioacetal) or competitive side reaction such as bromination, nitrene (from NO2) and α,α-dibromoolefine (with CHO/COMe) formation, and transesterification (with CO2Me/Et) taking place.

Chemoselective O-tert-butoxycarbonylation of hydroxy compounds using NaLaTiO4 as a heterogeneous and reusable catalyst

A facile, efficient and chemoselective protocol for O-tert-butoxycarbonylation of various hydroxy compounds has been developed using NaLaTiO4 (layered perovskite) as a novel catalyst. The catalyst showed remarkable activity and reusability affording high yields of the desired products under mild reaction conditions.

Novel 1,4-benzodiazepine derivatives with antiproliferative properties on tumor cell lines

Novel 1,4-benzodiazepine compounds were synthesized and evaluated for their ability to inhibit the proliferation of tumor cells. Some compounds revealed activities in the micromolar range and were more efficient than reference compound Ro 5-4864. Prelimin

Base-labile tert-butoxycarbonyl (Boc) group on phenols

Phenols are deprotected with weak bases from their tert-butoxycarbonyl (Boc) derivatives. Boc deprotection with bases can avoid side reactions during the deprotection with acids. We note the lability of the Boc to bases and are able to utilize it as a new cleavage condition for synthetic studies.