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Hydroboration-Oxidation of Alkenes

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.

Regioselectivity and Stereochemistry of Hydroboration

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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...

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

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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.

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The method to achieve α-brominated carboxylic acids using a mixture of phosphorus tribromide and bromine is known as the Hell–Volhard–Zelinski reaction. The reaction is catalyzed by phosphorus tribromide, which can be used directly or produced in situ from red phosphorus and bromine. The mechanism comprises PBr3 catalyzed conversion of acid to acid bromide and hydrogen bromide. The acid bromide enolizes to its enol form in the presence of HBr. The nucleophilic enol attacks the...

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Just like β-keto acids—which upon thermal decarboxylation form ketones—β-dicarboxylic acids undergo decarboxylation to generate monocarboxylic acids with the liberation of carbon dioxide.

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Updated: May 5, 2026

Synthesis of 1,2-Azaborines and the Preparation of Their Protein Complexes with T4 Lysozyme Mutants

Synthesis of 1,2-Azaborines and the Preparation of Their Protein Complexes with T4 Lysozyme Mutants

Published on: March 25, 2017

Decarboxylative borylation.

Chao Li¹, Jie Wang¹, Lisa M Barton¹

¹Department of Chemistry, The Scripps Research Institute (TSRI), La Jolla, CA 92037, USA.

Science (New York, N.Y.)

|April 15, 2017

Summary

This summary is machine-generated.

A new nickel-catalyzed reaction efficiently converts carboxylic acids into boronate esters. This method simplifies the synthesis of important alkyl boronic acid drugs and novel enzyme inhibitors.

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Area of Science:

Organic Chemistry
Medicinal Chemistry
Catalysis

Background:

Alkyl boronic acids and esters are valuable synthetic intermediates but their preparation is challenging.
Existing methods for synthesizing these compounds often involve complex procedures or limited scope.

Purpose of the Study:

To develop a simple, practical, and broad-scope method for preparing functionalized alkyl boronate esters.
To apply this new method to the synthesis of biologically relevant molecules, including pharmaceuticals and enzyme inhibitors.

Main Methods:

A nickel-catalyzed reaction was developed to convert carboxylic acid derivatives into boronate esters.
The reaction utilizes an activation strategy analogous to amide bond formation.
The method was applied to peptide synthesis and the preparation of α-amino boronic acids.

Main Results:

The reaction provides rapid access to densely functionalized alkyl boronate esters from abundant carboxylic substituents.
Synthesis of the alkyl boronic acid drugs Velcade and Ninlaro was facilitated.
A boronic acid analog of vancomycin was synthesized with high stereoselectivity.
Novel potent inhibitors of human neutrophil elastase with reversible covalent binding properties were discovered.

Conclusions:

The developed nickel-catalyzed reaction offers a versatile and efficient route to alkyl boronate esters.
This methodology significantly simplifies the synthesis of important pharmaceutical compounds and enables the discovery of new bioactive agents.
The method holds promise for broader applications in organic synthesis and drug discovery.