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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.
Examples of boronic esters Boronic ester Diol Structural formula Molar mass CAS number Boiling point (°C) Allylboronic acid pinacol ester: pinacol: 168.04: 72824-04-5: 50–53 (5 mmHg) Phenyl boronic acid trimethylene glycol ester: trimethylene glycol: 161.99: 4406-77-3: 106 (2 mm Hg) Diisopropoxymethylborane: isopropanol: 144.02 86595-27-9: ...
The pinacol reaction is extremely well-studied and tolerates many different reductants, including electrochemical syntheses.Variants are known for homo- and cross-coupling, intra- and inter-molecular reactions with appropriate diastereo- or enantioselectivity; [2] as of 2006, the only unsettled frontier was enantioselective cross-coupling of aliphatic aldehydes. [3]
It has the formula [(CH 3) 4 C 2 O 2 B] 2; the pinacol groups are sometimes abbreviated as "pin", so the structure is sometimes represented as B 2 pin 2. It is a colourless solid that is soluble in organic solvents. It is a commercially available reagent for making pinacol boronic esters for organic synthesis.
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 ...
Pinacol is a branched alcohol which finds use in organic syntheses. It is a diol that has hydroxyl groups on vicinal carbon atoms. A white solid that melts just above room temperature, pinacol is notable for undergoing the pinacol rearrangement in the presence of acid and for being the namesake of the pinacol coupling reaction .
Organotrifluoroborates are tolerant of air and moisture [1] and are easy to handle and purify. [2] They are often used in organic synthesis as alternatives to boronic acids (RB(OH) 2 ), boronate esters (RB(OR′) 2 ), and organoboranes (R 3 B), particularly for Suzuki-Miyaura coupling .
Pinacolborane is the borane with the formula (CH 3) 4 C 2 O 2 BH. Often pinacolborane is abbreviated HBpin. [1] It features a boron hydride functional group incorporated in a five-membered C 2 O 2 B ring. Like related boron alkoxides, pinacolborane is monomeric. It is a colorless liquid. [2] It features a reactive B-H functional group. [3]