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Upstream product

• 199999-46-7 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4-phenyl-1-phenylpropan-1-one 
• 100-42-5 styrene 
• 611-73-4 Benzoylformic acid 
• 1083-30-3 dihydrochalcone 

Relevant academic research and scientific papers

Triethylborane-initiated radical chain fluorination: A synthetic method derived from mechanistic insight

We offer a mild, metal-free sp3 C-H fluorination alternative using Selectfluor and a substoichiometric amount of triethylborane.an established radical initiator in the presence of O2. This radical-chain-based synthetic method is particularly noteworthy as an offspring of the insight gained from a mechanistic study of copper-promoted aliphatic fluorination, constructively turning O2 from an enemy to an ally. Furthermore, BEt3/O2 is a preferred initiator in industrial processes, as it is economical, is low in toxicity, and lends way to easier workup.

AgII-Mediated Synthesis of β-Fluoroketones by Oxidative Cyclopropanol Opening

A regioselective synthesis of β-fluorinated ketones by silver(II)-mediated ring opening is described. Commercially available AgF2 serves as both an oxidant and fluorine-atom source. A variety of β-fluorinated ketones are efficiently prepared from tertiary cyclopropanol precursors, offering a straightforward approach for the introduction of a fluorine atom at a remote site. Selectivity is observed in the site of bond cleavage, which leads to fluorination at the more substituted site. A radical mediated sequential homolytic C–C bond cleavage and C–F bond formation is suggested.

Silver-catalyzed radical fluorination of alkylboronates in aqueous solution

We report herein an efficient and general method for the deboronofluorination of alkylboronates. Thus, with the catalysis of AgNO3, the reactions of various alkylboronic acids or their pinacol esters with Selectfluor reagent in acidic aqueous solution afforded the corresponding alkyl fluorides under mild conditions. A broad substrate scope and wide functional group compatibility were observed. A radical mechanism is proposed for this site-specific fluorination.

Photocatalyzed benzylic fluorination: Shedding "light" on the involvement of electron transfer

The photocatalyzed oxidation of benzylic compounds by 1,2,4,5-tetracyanobenzene (TCB) in the presence of Selectfluor provides a synthetically efficient route to electron deficient, less substituted, and otherwise inaccessible benzylic fluorides. The virtue of this system is multifold: it is metal-free and mild, and the reagents are inexpensive. Mechanistically, the data suggest the intimate formation of intermediate radical cations in the key radical forming step, as opposed to a concerted hydrogen atom transfer process.

Silver-catalyzed decarboxylative acylfluorination of styrenes in aqueous media

A mild catalytic decarboxylative acylfluorination of styrenes with α-oxocarboxylic acids and Selectfluor is reported. This operationally simple and efficient method provides a fundamentally novel approach toward the synthesis of β-fluorinated 3-aryl ketones with a wide range of substrate scope.

Iron(II)-catalyzed benzylic fluorination

Direct C-F functionalization of benzylic sp3 C-H bonds is a synthetic challenge that has yet to be propitiously overcome. A mild, one-pot synthesis of monofluorinated benzylic substrates is reported with commercially available iron(II) acetylacetonate and Selectfluor in good to excellent yields and selectivity. A convenient route to β-fluorinated products of 3-aryl ketones is also highlighted, providing a synthetic equivalent to the difficult to accomplish conjugate addition of fluoride to α,β-unsaturated ketones.

Metal-catalyzed benzylic fluorination as a synthetic equivalent to 1,4-conjugate addition of fluoride

We explore in detail the iron-catalyzed benzylic fluorination of substrates containing aromatic rings and electron-withdrawing groups positioned β to one another, thus providing direct access to β-fluorinated adducts. This operationally convenient process can be thought of not only as a contribution to the timely problem of benzylic fluorination but also as a functional equivalent to a conjugate addition of fluoride, furnishing products in moderate to good yields and in excellent selectivity.