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Related Concept Videos

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.
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.
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.
Radical Anti-Markovnikov Addition to Alkenes: Overview01:25

Radical Anti-Markovnikov Addition to Alkenes: Overview

The addition of hydrogen bromide to alkenes in the presence of hydroperoxides or peroxides proceeds via an anti-Markovnikov pathway and yields alkyl bromides.
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...
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration02:34

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.

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Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
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Amine-directed hydroboration: scope and limitations.

Matthew Scheideman1, Guoqiang Wang, Edwin Vedejs

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

Journal of the American Chemical Society
|June 14, 2008
PubMed
Summary
This summary is machine-generated.

Iodine activation enables intramolecular hydroboration in amine boranes, offering regiochemical control. This method avoids retro-hydroboration and shows varying selectivity based on carbon chain length.

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Area of Science:

  • Organic Chemistry
  • Organometallic Chemistry

Background:

  • Hydroboration is a key organic transformation.
  • Controlling regioselectivity in hydroboration of unsaturated amine boranes is challenging.
  • Existing methods often lack precise control or involve harsh conditions.

Purpose of the Study:

  • To investigate iodine-induced intramolecular hydroboration of homoallylic and bis-homoallylic amine boranes.
  • To compare the regioselectivity of iodine-activated reactions with control experiments using tetrahydrofuran borane (THF·BH3).
  • To elucidate the reaction mechanism and the influence of tether length on selectivity.

Main Methods:

  • Activation of amine boranes using iodine.
  • Deuterium labeling studies to probe reaction pathways.
  • Comparative analysis of regioselectivity under different activation conditions and substrate structures.

Main Results:

  • Iodine activation promotes intramolecular hydroboration of homoallylic and bis-homoallylic amine boranes with good to excellent regiochemical control.
  • The reaction proceeds via an intramolecular mechanism, similar to a classical 4-center process, and is not reversible.
  • Regioselectivity is influenced by the carbon chain length, with shorter tethers favoring intermolecular reactions and longer tethers showing decreased selectivity.

Conclusions:

  • Iodine-mediated hydroboration offers a controlled method for functionalizing amine boranes.
  • The reaction mechanism is distinct from classical hydroboration and is sensitive to substrate structure.
  • This approach provides a valuable alternative for synthesizing specific organoboron compounds.