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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...
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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.
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A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
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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.
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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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Hydrolysis of acid halides is a nucleophilic acyl substitution reaction in which acid halides react with water to give carboxylic acids. The reaction occurs readily and does not require acid or a base catalyst.
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Iron-Catalysed C(sp2)-H Borylation Enabled by Carboxylate Activation.

Luke Britton1, Jamie H Docherty1, Andrew P Dominey2

  • 1EaStCHEM School of Chemistry, University of Edinburgh, Joseph Black Building, David Brewster Road, Edinburgh EH9 3FJ, UK.

Molecules (Basel, Switzerland)
|February 23, 2020
PubMed
Summary

Iron catalysts enable C(sp2)-H bond borylation of furans and thiophenes using blue light. This method offers an Earth-abundant alternative to iridium catalysts for synthesizing versatile boronic esters.

Keywords:
C-H functionalisationIronborylationcatalysisphotochemistrypinacolborane

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Sustainable Chemistry

Background:

  • Arene C(sp2)-H bond borylation is crucial for synthesizing boronic esters.
  • Iridium catalysts are effective but expensive and scarce.
  • Developing Earth-abundant catalysts is a key goal in sustainable chemistry.

Purpose of the Study:

  • To develop an iron-catalyzed C(sp2)-H borylation method.
  • To utilize readily available and air-stable reagents for in situ catalyst activation.
  • To explore the borylation of furans and thiophenes under blue light irradiation.

Main Methods:

  • In situ catalyst activation using air-stable reagents.
  • Iron-catalyzed C(sp2)-H borylation reactions.
  • Blue light irradiation as an energy source.
  • Preparation and characterization of key reaction intermediates.

Main Results:

  • Successful development of iron-catalyzed C(sp2)-H borylation of furans and thiophenes.
  • Demonstration of an in situ catalyst activation method.
  • Identification of key intermediates suggesting dual mechanistic pathways.
  • Insight into C-H metallation and iron boryl species formation.

Conclusions:

  • The developed iron-catalyzed method provides an efficient and sustainable alternative for boronic ester synthesis.
  • The study elucidates mechanistic insights into the iron-catalyzed borylation process.
  • This work expands the scope of Earth-abundant metal catalysis in C-H functionalization.