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Upstream product

• 145240-28-4 4-butylphenylboronic acid 
• 625458-85-7 2-(4-butylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 20651-67-6 4-butyliodobenzene 
• 6999-03-7 1-bromo-4-(trimethylsilyl)benzene 
• 106-37-6 1.4-dibromobenzene 
• 81631-74-5 4-n-butyl-1-trimethylsilylbenzene 

Relevant academic research and scientific papers

Copper-mediated fluorination of aryl iodides

The synthesis of aryl fluorides has been studied intensively because of the importance of aryl fluorides in pharmaceuticals, agrochemicals, and materials. The stability, reactivity, and biological properties of aryl fluorides can be distinct from those of the corresponding arenes. Methods for the synthesis of aryl fluorides, however, are limited. We report the conversion of a diverse set of aryl iodides to the corresponding aryl fluorides. This reaction occurs with a cationic copper reagent and silver fluoride. Preliminary results suggest this reaction is enabled by a facile reductive elimination from a cationic arylcopper(III) fluoride.

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.

Copper-mediated fluorination of arylboronate esters. Identification of a Copper(III) fluoride complex

A method for the direct conversion of arylboronate esters to aryl fluorides under mild conditions with readily available reagents is reported. Tandem reactions have also been developed for the fluorination of arenes and aryl bromides through arylboronate ester intermediates. Mechanistic studies suggest that this fluorination reaction occurs through facile oxidation of Cu(I) to Cu(III), followed by rate-limiting transmetalation of a bound arylboronate to Cu(III). Fast C-F reductive elimination is proposed to occur from an aryl-copper(III)-fluoride complex. Cu(III) intermediates have been generated independently and identified by NMR spectroscopy and ESI-MS.

The carbon-silicon bond cleavage of organosilicon compounds in supercritical water

Arylsilanes, alkenylsilanes, allylic silanes, and alkylsilanes were found to undergo extremely facile and rapid C-Si bond cleavage in supercritical water. Rapid C-Si bond cleavage occurred even with robust unactivated tetraalkylsilanes. The control experiments revealed the dramatic difference between the supercritical and subcritical conditions, and that between supercritical water and supercritical methanol, attesting to a unique reactivity of supercritical water in C-Si bond cleavage. It was also found that acids, such as HCl, HBr, and H2SO4, promote C-Si bond cleavage in supercritical water.

Efficient and rapid C-Si bond cleavage in supercritical water

Arylsilanes, alkenylsilanes, allylic silanes, and alkylsilanes were found to undergo extremely facile and rapid C-Si bond cleavage in supercritical water. The rapid C-Si bond cleavage occurred even with robust unactivated tetraalkylsilanes. The control experiments revealed the dramatic difference between supercritical and subcritical conditions and that between supercritical water and supercritical methanol, attesting to a unique reactivity of supercritical water in C-Si bond cleavage. Copyright