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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.

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.

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.

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...

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Updated: May 25, 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

High-Throughput Enabled Iridium-Catalyzed C-H Borylation Platform for Late-Stage Functionalization.

Janis M Zakis^1,2, Rebeka A Lipina¹, Sharon Bell¹

¹Research Chemistry, Syngenta Crop Protection AG, Schaffhauserstrasse 101, AG 4332 Stein, Switzerland.

ACS Catalysis

|February 27, 2025

Summary

A new high-throughput platform rapidly optimizes C-H borylation, minimizing reagents. This enables efficient synthesis of diverse bioactive compound derivatives for drug discovery and agrochemical research.

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Last Updated: May 25, 2025

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Published on: June 20, 2014

Area of Science:

Organic Chemistry
Catalysis
Medicinal Chemistry

Background:

Late-stage functionalization is crucial for drug discovery.
C-H borylation offers a versatile route for modifying complex molecules.
Efficient optimization of C-H borylation protocols is needed.

Purpose of the Study:

To develop a high-throughput platform for optimizing regiodivergent C-H borylation.
To enable rapid evaluation of various borylation catalysts and conditions.
To minimize starting material requirements for reaction optimization.

Main Methods:

Implemented a dedicated high-throughput reaction optimization platform.
Utilized an informer library approach for comparative analysis.
Applied the workflow to diverse fragment-like compounds, pharmaceuticals, and agrochemicals.

Main Results:

Successfully optimized and evaluated multiple C-H borylation protocols.
Isolated 36 derivatives of bioactive compounds, demonstrating practicality.
Identified surprising reactivity patterns and the effectiveness of ligand-free borylation.

Conclusions:

High-throughput platforms accelerate the optimization of C-H borylation.
This approach enhances the utility of late-stage functionalization in pharmaceutical and agrochemical research.
The study revealed broader applicability of existing C-H borylation catalysts.