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Related Concept Videos

Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis01:13

Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis

Hydrolysis of esters under acidic conditions proceeds through a nucleophilic acyl substitution. In the presence of excess water, the reaction proceeds in a reversible manner, forming carboxylic acids and alcohols.
During hydrolysis, the ester is first activated towards nucleophilic attack through the protonation of the carboxyl oxygen atom by the acid catalyst. The protonation makes the ester carbonyl carbon more electrophilic. In the next step, water acts as a nucleophile and adds to the...
Regioselective Formation of Enolates01:33

Regioselective Formation of Enolates

As depicted in the figure below, the unsymmetrical ketones can form two possible enolates: less substituted or more substituted enolates. Usually, the thermodynamic enolates are formed from the more substituted α-carbon atom, while the kinetic enolates are formed faster by deprotonation from the less substituted position. The thermodynamic enolates have lower energy, so they are more stable. But the energy required to form kinetic enolates is less.
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
Alkylation of β-Diester Enolates: Malonic Ester Synthesis01:14

Alkylation of β-Diester Enolates: Malonic Ester Synthesis

Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.

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Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides
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Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides

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Goldilocks boronic esters: optimized properties through understanding hydrolysis kinetics.

Reyner D Vargas1, Samantha S Cox1, James O Larkin1

  • 1Department of Chemistry, Rice University, Bioscience Research Collaborative 6100 Main Street Houston Texas 77005 USA zb1@rice.edu.

Chemical Science
|June 5, 2026
PubMed
Summary
This summary is machine-generated.

This study introduces tunable boronic esters using diols for controlled synthesis and dynamic covalent chemistry. Researchers developed a practical dataset for selecting boronic ester protecting groups for predictable, mild, and temporally controlled access to boronic acids.

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Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators

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Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
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Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators

Published on: November 27, 2015

Area of Science:

  • Organic Chemistry
  • Supramolecular Chemistry
  • Materials Science

Background:

  • Boronic acids reversibly form boronic esters with diols, useful as protecting groups in synthesis and in dynamic covalent chemistry.
  • Limited quantitative structure-function data hinders optimal selection/design of boronic esters for specific applications.
  • Existing methods lack predictable control over boronic ester stability and hydrolysis rates.

Purpose of the Study:

  • To systematically investigate structure-function relationships of 1,2-diol derived boronic esters.
  • To develop boronic esters with tunable hydrolytic behavior and simple one-pot formation.
  • To provide a practical dataset for rational selection of boronic ester protecting groups.

Main Methods:

  • Systematic study of a family of 1,2-diols with various boronic acids (aryl, heteroaryl, bioactive).
  • Modulation of hydrolysis rates by varying diol structure, electronics, and pH.
  • Assessment of silica compatibility and performance under biocompatible conditions.

Main Results:

  • Demonstrated tunable hydrolytic behavior of boronic esters across a broad range.
  • Achieved simple one-pot formation of diverse boronic esters.
  • Established predictable control over hydrolysis rates by diol structure, electronics, and pH.
  • Maintained silica compatibility for practical applications.

Conclusions:

  • Developed a practical dataset for rationally selecting boronic ester protecting groups.
  • Enabled predictable, mild, and temporally controlled access to free boronic acids under biocompatible conditions.
  • Provided a synthetic solution for challenges in complex boronic acid preparation.