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Protodeboronation is a well-known undesired side reaction, and frequently associated with metal-catalysed coupling reactions that utilise boronic acids (see Suzuki reaction). [1] For a given boronic acid, the propensity to undergo protodeboronation is highly variable and dependent on various factors, such as the reaction conditions employed and ...
Phenylboronic acid can also be regioselectively halodeboronated using aqueous bromine, chlorine, or iodine: [10] PhB(OH) 2 + Br 2 + H 2 O → PhBr + B(OH) 3 + HBr. Boronic esters result from the condensation of boronic acids with alcohols. This transformation is simply the replacement of the hydroxyl group by alkoxy or aryloxy groups. [4] This ...
Removal of the BOC group in amino acids can be accomplished with strong acids such as trifluoroacetic acid in dichloromethane, or with HCl in methanol. [2] [3] [4] A complication may be the tendency of the t-butyl cation intermediate to alkylate other nucleophiles; scavengers such as anisole or thioanisole may be used.
The general structure of a boronic acid, where R is a substituent. A boronic acid is an organic compound related to boric acid (B(OH) 3) in which one of the three hydroxyl groups (−OH) is replaced by an alkyl or aryl group (represented by R in the general formula R−B(OH) 2). [1]
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]
In a weakly acidic condition, fairly concentrated (35%) H 2 O 2 solution undergoes a rapid oxidative reaction with no competitive reduction reaction of HClO 2 to form HOCl. HClO 2 + H 2 O 2 → HOCl + O 2 + H 2 O. Chlorine dioxide reacts rapidly with H 2 O 2 to form chlorous acid. 2ClO 2 + H 2 O 2 → 2HClO 2 + O 2
A widely used peroxy acid for this reaction is meta-chloroperoxybenzoic acid (m-CPBA), due to its stability and good solubility in most organic solvents. [1] [3] The reaction is performed in inert solvents (C 6 H 14, C 6 H 6, CH 2 Cl 2, CHCl 3, CCl 4) between -10 and 60 °C with the yield of 60-80%. An illustrative example is the epoxidation of ...
The Koch reaction is an organic reaction for the synthesis of tertiary carboxylic acids from alcohols or alkenes and carbon monoxide.Some commonly industrially produced Koch acids include pivalic acid, 2,2-dimethylbutyric acid and 2,2-dimethylpentanoic acid. [1]