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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]
This protocol has proved useful in the cross-coupling of some notoriously unstable boronic acids, such as the 2-pyridine boronic acid. [ 16 ] [ 17 ] This ensures that the boronic acid concentration is low during the cross-coupling reaction, which in turn minimises the potential for side reactions.
Formyl functional group is shown in blue. Formylation refers to any chemical processes in which a compound is functionalized with a formyl group (-CH=O). In organic chemistry, the term is most commonly used with regards to aromatic compounds (for example the conversion of benzene to benzaldehyde in the Gattermann–Koch reaction).
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.
[3] Trimethyl borate is a popular borate ester used in organic synthesis. Borate esters form spontaneously when treated with diols such as sugars and the reaction with mannitol forms the basis of a titrimetric analytical method for boric acid. Metaborate esters show considerable Lewis acidity and can initiate epoxide polymerization reactions. [4]
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]
3-Methylthiophene is an organosulfur compound with the formula CH 3 C 4 H 3 S. It is a colorless, flammable liquid. It can be produced by sulfidation of 2-methylsuccinate. [1] Like its isomer 2-methylthiophene, its commercial synthesis involvess vapor-phase dehydrogenation of
Hydrolysis then results in the boronic acid (R 2 BOH). [5] Trialkylborates [(RO) 3 B] or trialkoxyboroxine [(ROBO) 3] can be reduced to borinic acid by us of a Grignard reagent. Grignard reagents can also reduce a boronic ester [RB(OR') 2] to a borinic ester. [5] Bu 3 B + N2CHCOR → BuCH=C(R)OBBu 2 Bu 3 B + CH2=CHCOCH 3 → BuCH 2 CH=C(CH 3)OBBu 2