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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 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.
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 amine is condensed with the carbonyl followed by addition of the boronic acid . [1] Alpha amino acid synthesis. One of the most attractive features of the Petasis reaction is the stability of the vinyl boronic acids. With the advent of the Suzuki coupling, many are commercially available. organoboronic acid synthesis. Other methods of ...
The boron reagent is converted to boric acid. The reaction was originally described by H.C. Brown in 1957 for the conversion of 1-hexene into 1-hexanol. [3] Hexanol synthesis. Knowing that the group containing the boron will be replaced by a hydroxyl group, it can be seen that the initial hydroboration step determines the regioselectivity.
An alternate pathway consists of the formation of the benzylboronic acid via a zwitterionic intermediate, followed by protodeboronation of the benzylboronic acid under basic conditions, which results in the final reductive product. Reaction proceeds via a diazo intermediate and then can take one of two equally plausible mechanistic pathways.
Boronic acid self-condensation or condensation with diols is a well-documented dynamic covalent reaction. The boronic acid condensation has the characteristic of forming two dynamic bonds with various substrates. This is advantageous when designing systems where high rigidity is desired, such as 3-D cages and COFs. [10]
The Suzuki reaction or Suzuki coupling is an organic reaction that uses a palladium complex catalyst to cross-couple a boronic acid to an organohalide. [1] [2] [3] It was first published in 1979 by Akira Suzuki, and he shared the 2010 Nobel Prize in Chemistry with Richard F. Heck and Ei-ichi Negishi for their contribution to the discovery and development of noble metal catalysis in organic ...