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Related Concept Videos

Hydrolysis of Chlorobenzene to Phenol: Dow Process01:10

Hydrolysis of Chlorobenzene to Phenol: Dow Process

Simple aryl halides do not react with nucleophiles under normal conditions. However, the reaction can proceed under drastic conditions involving high temperatures and high pressure to give the substituted products. For example, chlorobenzene is converted to phenol using aqueous sodium hydroxide at 350 °C under high pressure by the Dow process. The reaction follows an elimination-addition mechanism involving a benzyne intermediate. Here, the chloride ion is eliminated to generate the benzyne...
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.
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.
α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction01:15

α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction

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 bromine molecule...
Preparation of Alcohols via Addition Reactions02:15

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...

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Related Experiment Video

Updated: May 14, 2026

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
08:56

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

Published on: November 30, 2022

P-directed borylation of phenols.

Clément Cazorla1, Timothy S De Vries, Edwin Vedejs

  • 1Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, USA.

Organic Letters
|February 1, 2013
PubMed
Summary

A new method activates aryl phosphinite boranes using HNTf(2) to form heterocyclic intermediates. These intermediates yield valuable potassium aryl trifluoroborate salts for palladium-catalyzed cross-coupling reactions.

Area of Science:

  • Organometallic Chemistry
  • Synthetic Organic Chemistry

Background:

  • Aryl boranes are versatile synthetic intermediates.
  • Palladium-catalyzed cross-coupling reactions are crucial for C-C bond formation.

Purpose of the Study:

  • To develop a novel method for synthesizing potassium aryl trifluoroborate salts.
  • To explore the utility of these salts in palladium-catalyzed coupling reactions.

Main Methods:

  • Activation of aryl di-isopropylphosphinite boranes using HNTf(2).
  • Formation of heterocyclic intermediates.
  • Treatment with potassium hydrogen difluoride (KHF(2)) to yield trifluoroborate salts.
  • Palladium-catalyzed Suzuki-Miyaura coupling under modified Molander conditions.

Main Results:

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[(DPEPhos)(bcp)Cu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
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[(DPEPhos)(bcp)Cu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst

Published on: May 21, 2019

Related Experiment Videos

Last Updated: May 14, 2026

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
08:56

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

Published on: November 30, 2022

[(DPEPhos)(bcp)Cu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
09:12

[(DPEPhos)(bcp)Cu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst

Published on: May 21, 2019

  • Successful synthesis of heterocyclic intermediates from aryl phosphinite boranes.
  • Efficient generation of phenolic potassium aryl trifluoroborate salts.
  • Demonstrated utility of the trifluoroborate salts in Pd-catalyzed coupling with aryl iodides.
  • Identified the necessity of removing KNTf(2) byproduct for optimal coupling efficiency.

Conclusions:

  • A new synthetic route to potassium aryl trifluoroborate salts has been established.
  • These trifluoroborate salts are effective coupling partners in palladium-catalyzed reactions.
  • Optimization of reaction conditions, including byproduct removal, is critical for successful cross-coupling.