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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.

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.

Preparation of Alcohols via Addition Reactions

Preparation of Alcohols via Addition Reactions

Overview
The acid-catalyzed addition of water to the double bond of alkenes is a large-scale industrial method used to synthesize low-molecular-weight alcohols. An acidic atmosphere is required to allow the hydrogen in the water molecule to act as an electrophile and attack the double bond in an alkene. The addition of a proton to the double bond creates a carbocation intermediate. The proton preferentially bonds to the less substituted end of the double bond to create a more stable carbocation...

Regioselectivity and Stereochemistry of Hydroboration

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...

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

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.

ortho–para-Directing Activators: –CH3, –OH, –&NoBreak;NH2, –OCH3

ortho–para-Directing Activators: –CH₃, –OH, –⁠NH₂, –OCH₃

All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the...

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Related Experiment Video

Updated: May 16, 2025

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Published on: November 30, 2022

Boron-Based Functionalities Enhance, the Potency of 2,5-Dimethylfuran-Based IDO1 Inhibitors.

Thomas J C Carraro¹, Samrat Dasgupta¹, Jacqueline Ku²

¹School of Chemistry, The University of Sydney, Sydney, NSW, 2006, Australia.

Chembiochem : a European Journal of Chemical Biology

|April 4, 2025

Summary

New boron-based compounds show promise as indoleamine-2,3-dioxygenase 1 (IDO1) inhibitors. These novel molecules, particularly closo-carboranes, offer improved potency for potential therapeutic applications in inflammation and disease.

Keywords:

boron carboranes drug discoveries indoleamine‐2,3‐dioxygenase‐1 inhibitors

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Surface Functionalization of Metal-Organic Frameworks for Improved Moisture Resistance

Surface Functionalization of Metal-Organic Frameworks for Improved Moisture Resistance

Published on: September 5, 2018

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Last Updated: May 16, 2025

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Published on: November 30, 2022

Chemical Inactivation of the E3 Ubiquitin Ligase Cereblon by Pomalidomide-based Homo-PROTACs

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Published on: May 15, 2019

Surface Functionalization of Metal-Organic Frameworks for Improved Moisture Resistance

Surface Functionalization of Metal-Organic Frameworks for Improved Moisture Resistance

Published on: September 5, 2018

Area of Science:

Medicinal Chemistry
Enzymology
Immunology

Background:

Indoleamine-2,3-dioxygenase 1 (IDO1) is a key enzyme in tryptophan metabolism, crucial in regulating immune responses during inflammation and disease.
IDO1 activity is implicated in various pathological conditions, making it a significant therapeutic target.

Purpose of the Study:

To design and synthesize novel indoleamine-2,3-dioxygenase 1 (IDO1) inhibitors.
To explore the potential of boron-based functional groups in developing potent IDO1 inhibitors.

Main Methods:

Synthesis of novel compounds based on a 2,5-dimethylfuran framework.
Incorporation of diverse boron-based functional groups, including closo-carboranes, boronic acids/esters, and benzoxaboroles.
In vitro enzymatic assays using human recombinant IDO1 to determine inhibitory activity (IC50 values).

Main Results:

Novel boron derivatives exhibited low micromolar affinity for human recombinant IDO1, with IC50 values ranging from 8 to 60 μM.
Closo-carborane compounds demonstrated superior inhibitory potency compared to their phenyl analogues.
Inhibition of IDO1 enzyme activity increased by up to approximately 80% with closo-carborane derivatives.

Conclusions:

Boron-based functional groups can be effectively incorporated into drug scaffolds to yield potent IDO1 inhibitors.
Closo-carborane derivatives represent a promising class of compounds for targeting IDO1 in inflammatory and disease contexts.
These findings provide a foundation for the development of new therapeutic agents modulating IDO1 activity.