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Related Concept Videos

Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

11.8K
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.
11.8K
Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

9.6K
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.
9.6K
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

21.6K
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.
21.6K
Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

2.3K
Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation reactions,...
2.3K
Preparation of Alcohols via Addition Reactions02:15

Preparation of Alcohols via Addition Reactions

7.9K
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...
7.9K
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

7.7K
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.
7.7K

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Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
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Tris(2,4,6-trifluorophenyl)borane: An Efficient Hydroboration Catalyst.

James R Lawson1, Lewis C Wilkins1, Rebecca L Melen1

  • 1School of Chemistry, Cardiff University, Main Building, Park Place, Cardiff, Cymru/Wales, CF10 3AT, UK.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|July 8, 2017
PubMed
Summary
This summary is machine-generated.

A new metal-free catalyst, tris(2,4,6-trifluorophenyl)borane, efficiently catalyzes the 1,2-hydroboration of alkynes, aldehydes, and imines. This versatile catalyst enables the synthesis of over 50 borylated products under mild conditions.

Keywords:
Lewis acidsboroncatalysishydroborationmetal-free

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Organoboron Chemistry

Background:

  • 1,2-hydroboration is a key transformation in organic synthesis.
  • Development of efficient and selective catalysts for hydroboration is ongoing.
  • Metal-free catalysts offer potential advantages in terms of cost and environmental impact.

Purpose of the Study:

  • To explore the catalytic activity of tris(2,4,6-trifluorophenyl)borane in 1,2-hydroboration reactions.
  • To demonstrate the broad substrate scope and efficiency of this metal-free catalyst.
  • To showcase the synthetic utility of the resulting borylated products.

Main Methods:

  • Utilized tris(2,4,6-trifluorophenyl)borane as a metal-free catalyst.
  • Investigated the hydroboration of various unsaturated substrates including alkynes, aldehydes, and imines.
  • Optimized reaction conditions, focusing on catalyst loading and ambient temperature.

Main Results:

  • Achieved efficient 1,2-hydroboration of a wide range of alkynes, aldehydes, and imines.
  • Synthesized over 50 distinct borylated products with high yields.
  • Demonstrated successful reactions using low catalyst loadings under ambient conditions.
  • Showcased the facile hydrolysis of resulting pinacol boronate esters to alcohols and amines, and vinyl boranes from alkynes.

Conclusions:

  • Tris(2,4,6-trifluorophenyl)borane is a highly effective metal-free catalyst for 1,2-hydroboration.
  • The catalyst exhibits broad substrate scope and operates efficiently under mild conditions.
  • The borylated products are versatile synthetic intermediates for organic chemists.