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Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

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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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Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

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

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

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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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Preparation of Alcohols via Addition Reactions02:15

Preparation of Alcohols via Addition Reactions

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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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Radical Anti-Markovnikov Addition to Alkenes: Mechanism01:17

Radical Anti-Markovnikov Addition to Alkenes: Mechanism

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The reaction of hydrogen bromide with alkenes in the presence of hydroperoxides or peroxides proceeds via anti-Markovnikov addition. The radical chain reaction comprises initiation, propagation, and termination steps.
The mechanism starts with chain initiation, which involves two steps. In the first chain initiation step, a weak peroxide bond is homolytically cleaved upon mild heating to form two alkoxy radicals. In the second initiation step, a hydrogen atom is abstracted by the alkoxy...
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Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

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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.
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...
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Related Experiment Video

Updated: Jul 28, 2025

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

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Olefin hydroboration catalyzed by an iron-borane complex.

Laura A Grose1, Darren Willcox1

  • 1Department of Chemistry, University of Manchester, Oxford Road, Manchester, M13 9PL, UK. darren.willcox@manchester.ac.uk.

Chemical Communications (Cambridge, England)
|May 30, 2023
PubMed
Summary

An iron(0) complex catalyzes olefin hydroboration. This reaction efficiently converts olefins into valuable organic compounds using a novel iron-based catalyst system.

Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Organic Synthesis

Background:

  • Iron complexes offer a sustainable alternative to precious metal catalysts.
  • The development of efficient catalytic systems for hydroboration is crucial for organic synthesis.

Purpose of the Study:

  • To investigate the reactivity of a specific iron(0) complex with boranes.
  • To evaluate the catalytic potential of this iron complex in olefin hydroboration.

Main Methods:

  • Synthesis and characterization of the iron(0) complex [(DPBPh)Fe2-(μ-1,2-N2)] (A).
  • Reaction of complex A with HBpin to form complex B via oxidative addition.
  • Testing complex A as a pre-catalyst for the hydroboration of various olefins under neat conditions.

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Main Results:

  • The iron(0) complex A successfully reacted with HBpin, yielding complex B through oxidative addition of the H-B bond.
  • Complex A demonstrated high efficacy as a pre-catalyst for olefin hydroboration.
  • The hydroboration reactions proceeded in synthetically useful yields, typically exceeding 80%, under neat conditions.

Conclusions:

  • The studied iron(0) complex is a potent pre-catalyst for olefin hydroboration.
  • This catalytic system provides an efficient route to valuable hydroborated products.
  • The use of iron offers a cost-effective and sustainable approach to this important transformation.