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Related Concept Videos

Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

9.8K
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.
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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 stereochemistry.
8.8K
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

19.5K
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.
19.5K
Preparation of Alcohols via Addition Reactions02:15

Preparation of Alcohols via Addition Reactions

6.8K
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...
6.8K
Radical Oxidation of Allylic and Benzylic Alcohols01:21

Radical Oxidation of Allylic and Benzylic Alcohols

2.5K
Activated manganese(IV) oxide can selectively oxidize allylic and benzylic alcohols via a radical intermediate mechanism. Primary allylic alcohols are oxidized to aldehydes, while secondary allylic alcohols yield ketones. The redox reaction of potassium permanganate with an Mn(II) salt such as manganese sulfate (under either alkaline or acidic conditions), followed by thorough drying, yields the oxidizing agent: activated MnO2. While MnO2 is insoluble in the solvents used for the reaction, the...
2.5K
Oxidation of Alkenes: Syn Dihydroxylation with Potassium Permanganate02:21

Oxidation of Alkenes: Syn Dihydroxylation with Potassium Permanganate

14.5K
Alkenes can be dihydroxylated using potassium permanganate.  The method encompasses the reaction of an alkene with a cold, dilute solution of potassium permanganate under basic conditions to form a cis-diol along with a brown precipitate of manganese dioxide.
14.5K

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Updated: Nov 8, 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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Manganese-Catalyzed Hydroborations with Broad Scope.

Pradip Ghosh1, Axel Jacobi von Wangelin1

  • 1Dept. of Chemistry, University of Hamburg, Martin Luther King Pl 6, 20146, Hamburg, Germany.

Angewandte Chemie (International Ed. in English)
|April 24, 2021
PubMed
Summary
This summary is machine-generated.

This study introduces a simple manganese catalyst for reducing various oxidized compounds like carbonyls and carbonates. This new method offers a facile and broad-scope approach for chemical synthesis and depolymerization.

Keywords:
amidescarbon dioxidecarbonatesdepolymerizationhydroborationmanganese

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Area of Science:

  • Synthetic Chemistry
  • Catalysis
  • Green Chemistry

Background:

  • Reductive transformations are crucial for chemical synthesis and valorization.
  • Catalytic hydrofunctionalization often requires facile setups and liquid reducing agents.
  • Metal-catalyzed hydroborations are effective for reducing C=X electrophiles.

Purpose of the Study:

  • To develop a facile and broad-scope reduction method for various oxidized compounds.
  • To utilize an inexpensive manganese pre-catalyst for reductive transformations.
  • To explore the application of this method in depolymerization processes.

Main Methods:

  • Employed manganese bis(hexamethyldisilazide) [Mn(hmds)2] as an inexpensive pre-catalyst.
  • Investigated the reduction of diverse functional groups including carbonyls, carboxylates, pyridines, carbodiimides, and carbonates.
  • Conducted reactions under very mild conditions.

Main Results:

  • Achieved facile and broad-scope reduction of multiple functional groups.
  • Demonstrated the effectiveness of the Mn(hmds)2 pre-catalyst under mild conditions.
  • Successfully applied the developed method to depolymerization reactions.

Conclusions:

  • The reported manganese-catalyzed reaction provides an efficient and accessible route for reductive transformations.
  • This method broadens the scope of catalytic hydrofunctionalization and offers potential for sustainable chemical valorization.
  • The applicability to depolymerization highlights its utility in materials science.