1583286-47-8

Usage

Type of compound

Boronic ester derivative It is derived from a boronic acid and an alcohol, resulting in a compound with a boron atom bonded to two oxygen atoms.

Boron atom

Bonded to two oxygen atoms, forming a four-membered 1,3,2-dioxaborolane ring.

Fluorine-substituted phenyl group

A phenyl group (a six-membered aromatic ring) with a fluorine atom at the 3-position and a methyl group at the 5-position.

Four methyl groups

Attached to the carbon atoms adjacent to the boron atom.

Uses

Organic synthesis and medicinal chemistry The compound is commonly used as a reagent in various organic reactions, such as cross-coupling reactions and Suzuki-Miyaura coupling.

Stability and compatibility

The compound is known for its stability and compatibility with various reaction conditions, making it a valuable reagent for a wide range of organic transformations.

Applications

Synthesis of pharmaceuticals, agrochemicals, and materials science Due to its unique structure and reactivity, the compound is a valuable tool in the synthesis of various products in different fields.

Upstream product

• 352-70-5 m-Fluorotoluene 
• 73183-34-3 bis(pinacol)diborane 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 491862-84-1 1-fluoro-3-iodo-5-methylbenzene 

Relevant academic research and scientific papers

Radical Metal-Free Borylation of Aryl Iodides

A simple metal-free borylation of aryl iodides mediated by a fluoride sp 2 -sp 3 diboron adduct is described. The reaction conditions are compatible with various functional groups. Electronic effects of substituents do not affect the borylation while steric hindrance does. The reaction proceeds via a radical mechanism in which pyridine serves to stabilize the boryl radicals, generated in situ.

POP-rhodium-promoted C-H and B-H bond activation and C-B bond formation

The square-planar monohydride complex RhH{xant(PiPr2)2} (1; xant(PiPr2)2 = 9,9-dimethyl-4,5-bis(diisopropylphosphino)xanthene) activates C-H bonds of arenes. Heating of benzene solutions of 1 at 80 °C affords RhPh{xant(PiPr2)2} (2). Under the same conditions, toluene gives Rh(m-tolyl){xant(PiPr2)2} (3a) and Rh(p-tolyl){xant(PiPr2)2} (3b) in a 78:22 molar ratio, whereas m-xylene leads to Rh(C6H3-3,5-Me2){xant(PiPr2)2} (4). At room temperature, fluorobenzene and 1,3-difluorobenzene generate Rh(C6H4-2-F){xant(PiPr2)2} (5) and Rh(C6H3-2,6-F2){xant(PiPr2)2} (6), respectively. Complex 1 also promotes the B-H bond activation of pinacolborane (HBpin) and catecholborane (HBcat). The reactions initially give the trans-dihydride derivatives RhH2(BR2){xant(PiPr2)2} (BR2 = Bpin (7), Bcat (8)), which lose H2 to afford the square-planar Rh(BR2){xant(PiPr2)2} (BR2 = Bpin (9), Bcat (10)). Complex 2 reacts with HBpin to regenerate 1 and to give Ph-Bpin. Similarly, complex 9 regenerates 1 and gives Ph-Bpin by reaction with benzene. In agreement with these transformations, complex 1 catalyzes the direct C-H borylation of arenes. The selectivity of the process appears to be governed by the kinetic of the C-H bond activations of the arenes. Benzylic borylation is not observed for methylbenzenes. The first X-ray structure of a square-planar rhodium-boryl complex is also reported.

Rhodium-catalyzed intermolecular C-H silylation of arenes with high steric regiocontrol

Regioselective C-H functionalization of arenes has widespread applications in synthetic chemistry. The regioselectivity of these reactions is often controlled by directing groups or steric hindrance ortho to a potential reaction site. Here, we report a catalytic intermolecular C-H silylation of unactivated arenes that manifests very high regioselectivity through steric effects of substituents meta to a potential site of reactivity. The silyl moiety can be further functionalized under mild conditions but is also inert toward many common organic transformations, rendering the silylarene products useful building blocks. The remote steric effect that we observe results from the steric properties of both the rhodium catalyst and the silane.