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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

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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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Radical Substitution: Allylic Bromination01:27

Radical Substitution: Allylic Bromination

5.0K
In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...
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α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction01:15

α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction

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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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Preparation of Alcohols via Addition Reactions02:15

Preparation of Alcohols via Addition Reactions

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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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A General Three-Component Alkyl Petasis Boron-Mannich Reaction.

Chao Hu1, Jet Tsien1, Si-Jie Chen2

  • 1Department of Biochemistry, The University of Texas Southwestern Medical Center, 5323 Harry Hines Blvd, Dallas, Texas 75390, United States.

Journal of the American Chemical Society
|July 29, 2024
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Summary

This study introduces a new three-component reaction for synthesizing complex C(sp³)-rich amines, crucial for drug discovery. The method enables rapid generation of diverse amine libraries for identifying potential drug candidates.

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Area of Science:

  • Medicinal Chemistry
  • Organic Synthesis

Background:

  • Aryl amines are prevalent in biologically active molecules, with 37% of drug candidates featuring aromatic amines.
  • Advancements in medicinal chemistry emphasize C(sp³)-rich amines for improved drug properties.

Purpose of the Study:

  • To present a modular and straightforward three-component alkyl Petasis boron-Mannich (APBM) reaction.
  • To enable rapid access to diverse C(sp³)-rich complex amines.

Main Methods:

  • Utilized a three-component reaction involving amines, aldehydes, and alkyl boronates.
  • Adapted the transformation for high-throughput experimentation (HTE).

Main Results:

  • Demonstrated a modular and operationally simple APBM reaction.
  • Achieved rapid synthesis of diverse C(sp³)-rich complex amines via HTE.

Conclusions:

  • The APBM reaction provides efficient access to valuable amine building blocks.
  • This method accelerates the identification and development of new drug candidates.