94406-62-9

Upstream product

• 3972-65-4 1-bromo-4-tert-butylbenzene 
• 123324-71-0 p-tert-butylphenylboronic acid 
• 98-73-7 4-(1,1-dimethylethyl)benzoic acid 
• 253185-03-4 tert-butylbenzene 
• 811-98-3 d⁽⁴⁾-methanol 
• 122-78-1 phenylacetaldehyde 
• 66255-92-3 rac-(β,β-²H₂)styrene oxide 
• 96-09-3 styrene oxide 

Downstream Products

• 98-54-4 para-tert-butylphenol 
• 159591-91-0 2-deutero-4-tert-butylphenol 

Relevant academic research and scientific papers

Photoinduced catalyst-free deborylation-deuteration of arylboronic acids with D2O

Herein, novel photoinduced catalyst-free deborylation-deuteration of arylboronic acids with D2O is reported. The protocol was compatible with a variety of functionalities, including halogen, alkoxy, cyano, sulfonyl, trimethylsilyl, trifluoromethoxy, alkyl, hydroxyl, free acid, amide, and heteroaromatic rings. A wide range of deuterated products were obtained in good yields with a high level of deuteration. This method provides a green and practical pathway to synthesize deuterium labelled compounds under mild conditions.

Visible-Light-Photosensitized Aryl and Alkyl Decarboxylative Functionalization Reactions

Despite significant progress in aliphatic decarboxylation, an efficient and general protocol for radical aromatic decarboxylation has lagged far behind. Herein, we describe a general strategy for rapid access to both aryl and alkyl radicals by photosensitized decarboxylation of the corresponding carboxylic acids esters followed by their successive use in divergent carbon–heteroatom and carbon–carbon bond-forming reactions. Identification of a suitable activator for carboxylic acids is the key to bypass a competing single-electron-transfer mechanism and “switch on” an energy-transfer-mediated homolysis of unsymmetrical σ-bonds for a concerted fragmentation/decarboxylation process.

Hydro/deutero deamination of arylazo sulfones under metal and (photo)catalyst-free conditions

Hydrodeaminated and monodeuterated aromatics were obtained via a visible-light driven reaction of arylazo sulfones. Deuteration occurs efficiently in deuterated media such as isopropanol-d8 or in THF-d8/water mixtures and exhibits a high tolerance to the nature and the position of the aromatic substituents.

Metal-Free sp2-C-H Borylation as a Common Reactivity Pattern of Frustrated 2-Aminophenylboranes

C-H borylation is a powerful and atom-efficient method for converting affordable and abundant chemicals into versatile organic reagents used in the production of fine chemicals and functional materials. Herein we report a facile C-H borylation of aromatic and olefinic C-H bonds with 2-aminophenylboranes. Computational and experimental studies reveal that the metal-free C-H insertion proceeds via a frustrated Lewis pair mechanism involving heterolytic splitting of the C-H bond by cooperative action of the amine and boryl groups. The adapted geometry of the reactive B and N centers results in an unprecedentently low kinetic barrier for both insertion into the sp2-C-H bond and intramolecular protonation of the sp2-C-B bond in 2-ammoniophenyl(aryl)- or -(alkenyl)borates. This common reactivity pattern serves as a platform for various catalytic reactions such as C-H borylation and hydrogenation of alkynes. In particular, we demonstrate that simple 2-aminopyridinium salts efficiently catalyze the C-H borylation of hetarenes with catecholborane. This reaction is presumably mediated by a borenium species isoelectronic to 2-aminophenylboranes.

Nickel-catalyzed cross-coupling of styrenyl epoxides with boronic acids

Let's get multicatalytic! A Ni0 catalyst complexed with a biaryldialkyl monophosphine ligand facilitates C-C bond formation between styrenyl epoxides and aryl boronic acids (see scheme). X-ray analysis of a catalytically active nickel/ligand complex supports a redox pathway involving C sp 3-O bond activation. A variety of α-substituted alcohols were generated with good reaction efficiency by a multicatalytic sequence. Copyright