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Phenylboronic acid or benzeneboronic acid, abbreviated as PhB(OH) 2 where Ph is the phenyl group C 6 H 5 - and B(OH) 2 is a boronic acid containing a phenyl substituent and two hydroxyl groups attached to boron. Phenylboronic acid is a white powder and is commonly used in organic synthesis.
4-Trifluoromethylbenzaldehyde is the organofluorine compound with the formula CF 3 C 6 H 4 CHO. Two other isomers are also known: 2-trifluoromethylbenzaldehyde and 3-trifluoromethylbenzaldehyde. These compounds are derivatives of benzaldehyde with trifluoromethyl substituents.
The reagent was used in trifluoromethylation of a thiophenolate. S-(trifluoromethyl)dibenzothiophenium tetrafluoroborate is a commercially available and known trifluoromethylation reagent based on the same principle first documented in 1990. [64] [65] In this type of compound sulfur has been replaced by oxygen, selenium and tellurium.
The trifluoromethyl group has a significant electronegativity that is often described as being intermediate between the electronegativities of fluorine and chlorine. [1] For this reason, trifluoromethyl-substituted compounds are often strong acids, such as trifluoromethanesulfonic acid and trifluoroacetic acid.
Compounds of the type BR n (OR) 3-n are called borinic esters (n = 2), boronic esters (n = 1), and borates (n = 0). Boronic acids are key to the Suzuki reaction. Trimethyl borate, debatably not an organoboron compound, is an intermediate in sodium borohydride production.
Basic heteroaromatic boronic acids (boronic acids that contain a basic nitrogen atom, such as 2-pyridine boronic acid) display additional protodeboronation mechanisms. [4] A key finding shows the speciation of basic heteroaromatic boronic acids to be analogous to that of simple amino acids , with zwitterionic species forming under neutral pH ...
The mechanism of organotrifluoroborate-based Suzuki-Miyaura coupling reactions has recently been investigated in detail. The organotrifluoroborate hydrolyses to the corresponding boronic acid in situ, so a boronic acid can be used in place of an organotrifluoroborate, as long as it is added slowly and carefully. [7] [8]
A second and perhaps more valuable use of trifluorotoluene is as a synthetic intermediate. A derivative of trifluorotoluene, 3-aminobenzotrifluoride, is the precursor to the herbicide fluometuron. [3] It is synthesized via nitration followed by reduction to meta-H 2 NC 6 H 4 CF 3. This aniline is then converted to the urea.