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Related Concept Videos

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.
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.
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
Intramolecular Claisen Condensation of Dicarboxylic Esters: Dieckmann Cyclization01:13

Intramolecular Claisen Condensation of Dicarboxylic Esters: Dieckmann Cyclization

Dieckmann cyclization is an intramolecular Claisen condensation of diesters. The reaction occurs in the presence of a base and generates a cyclic β-ketoester as the final product. Commonly, 1, 6 and 1, 7-diesters are preferred substrates for the reaction since the generated five, and six-membered cyclic β-keto esters are particularly more stable.
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.
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.

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

Published on: November 30, 2022

A borylative cyclisation towards indole boronic esters.

Jianhui Huang1, Simon J F Macdonald, Joseph P A Harrity

  • 1Department of Chemistry, University of Sheffield, Sheffield, S3 7HF, UK.

Chemical Communications (Cambridge, England)
|October 22, 2010
PubMed
Summary
This summary is machine-generated.

Direct borylation of 2-alkynylanilines yields indole boronic esters. This palladium-catalyzed reaction merges cyclization with cross-coupling, enabling subsequent C-N bond formation for diverse applications.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Indole derivatives are crucial scaffolds in medicinal chemistry and materials science.
  • Efficient synthesis of functionalized indoles, particularly those bearing boronic esters, remains a key challenge.
  • Boronic esters are versatile synthetic intermediates for cross-coupling reactions.

Purpose of the Study:

  • To develop a direct and efficient method for synthesizing indole 3-boronic esters.
  • To explore the integration of borylation and cross-coupling reactions in a one-pot procedure.
  • To demonstrate the utility of the synthesized indole boronic esters in subsequent C-N bond forming reactions.

Main Methods:

  • Palladium-catalyzed borylation of 2-alkynylanilines.
  • One-pot sequential cyclization and cross-coupling reactions.
  • Characterization of indole 3-boronic ester products using standard spectroscopic techniques.

Main Results:

  • Successful synthesis of indole 3-boronic esters from readily available 2-alkynylanilines.
  • Demonstration of a one-pot procedure combining borylation and cross-coupling.
  • The synthesized indole boronic esters were effectively utilized in C-N bond forming reactions, showcasing their synthetic utility.

Conclusions:

  • 2-Alkynylaniline borylative cyclizations offer a direct route to valuable indole 3-boronic esters.
  • The developed methodology allows for streamlined synthesis through merged reaction sequences.
  • The resulting indole boronic esters serve as versatile building blocks for constructing complex nitrogen-containing molecules.