Ad
related to: quinoline 5 boronic acid pinacol esterbroadpharm.com has been visited by 10K+ users in the past month
Search results
Results from the WOW.Com Content Network
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.
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: ...
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 .
The boron atom of a boronic ester or acid is sp 2 hybridized possessing a vacant p orbital, enabling these groups to act as Lewis acids. The C–B bond of boronic acids and esters are slightly longer than typical C–C single bonds with a range of 1.55-1.59 Å.
The Miyaura borylation has shown to work for: Alkyl halides, [2] aryl halides, [1] [3] [4] aryl halides using tetrahydroxydiboron, [5] aryl halides using bis-boronic acid, [6] aryl triflates, [7] aryl mesylates, [8] vinyl halides, [9] vinyl halides of α,β-unsaturated carbonyl compounds, [10] and vinyl triflates.
MIDA boronate esters and organotrifluoroborates have both been utilised in "slow release" strategies, in which the reaction conditions are optimised to provide a slow release of boronic acid. This protocol has proved useful in the cross-coupling of some notoriously unstable boronic acids, such as the 2-pyridine boronic acid.
Oxidation of quinoline affords quinolinic acid (pyridine-2,3-dicarboxylic acid), a precursor to the herbicide sold under the name "Assert". [8] The reduction of quinoline with sodium borohydride in the presence of acetic acid is known to produce Kairoline A. [15] (C.f. Kairine) Several anti-malarial drugs contain quinoline substituents.
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]
Ad
related to: quinoline 5 boronic acid pinacol esterbroadpharm.com has been visited by 10K+ users in the past month