Related Experiment Video
Updated: Jan 8, 2026
08:56
Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
Published on: November 30, 2022
3.4K
Iridium-Catalyzed Para-Selective C─H Borylation via Attractive Weak Interactions
Saikat Guria1, Sayan Dey1, Buddhadeb Chattopadhyay1
1Department of Chemistry, Indian Institute of Science Education and Research Pune, Pune, Maharashtra, India.
Chemistry (Weinheim an Der Bergstrasse, Germany)
|December 13, 2025
Summary
Iridium-catalyzed C-H borylation is crucial for creating synthetic intermediates. New strategies use noncovalent interactions to selectively activate challenging para C-H bonds, advancing organic synthesis.
Area of Science:
- Organic Chemistry
- Catalysis
- Synthetic Methodology
Background:
- Organoboron compounds are versatile synthetic intermediates.
- Iridium-catalyzed C-H borylation offers high selectivity.
- Para C-H bond borylation is synthetically challenging due to steric hindrance.
Purpose of the Study:
- To provide a comprehensive overview of iridium-catalyzed para-selective C-H borylation strategies.
- To highlight the role of weak noncovalent interactions in activating para C-H bonds.
- To discuss current progress, challenges, and future prospects in this field.
Main Methods:
- Review of recent literature on iridium-catalyzed C-H borylation.
- Categorization of strategies based on the type of noncovalent interactions employed.
- Analysis of reaction mechanisms and selectivity control.
Main Results:
- Development of diverse strategies utilizing noncovalent interactions for para C-H borylation.
- Demonstration of successful activation of sterically hindered para C-H bonds.
- Advancement in achieving high selectivity in borylation reactions.
Conclusions:
- Weak noncovalent interactions are key to overcoming challenges in para C-H borylation.
- Significant progress has been made in iridium-catalyzed para-selective C-H borylation.
- Further research is needed to explore novel interactions and expand substrate scope.
Related Concept Videos
02:36Regioselectivity and Stereochemistry of Hydroboration
9.3K
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 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.
9.3K
02:35Regioselectivity of Electrophilic Additions-Peroxide Effect
10.1K
In the presence of organic peroxides, the addition of hydrogen bromide to an alkene yields the isomer that is not predicted by Markovnikov’s rule. For example, the addition of hydrogen bromide to 2-methylpropene in the presence of peroxides gives 1-bromo-2-methylpropane. This addition reaction proceeds via a free radical mechanism, which reverses the regioselectivity. The free radical reaction mechanism involves three stages: initiation, propagation, and termination.
10.1K
02:47Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
20.6K
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.
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.
20.6K
03:08Hydroboration-Oxidation of Alkenes
11.0K
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.
11.0K
01:25Radical Anti-Markovnikov Addition to Alkenes: Overview
4.0K
The addition of hydrogen bromide to alkenes in the presence of hydroperoxides or peroxides proceeds via an anti-Markovnikov pathway and yields alkyl bromides.
4.0K
02:17Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule
16.1K
If a set of reactants can yield multiple constitutional isomers, but one of the isomers is obtained as the major product, the reaction is said to be regioselective. In such reactions, bond formation or breaking is favored at one reaction site over others.
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...
16.1K