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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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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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Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

8.1K
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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Preparation of Alcohols via Addition Reactions02:15

Preparation of Alcohols via Addition Reactions

6.2K
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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α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction01:15

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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...
3.0K
Amides to Carboxylic Acids: Hydrolysis01:28

Amides to Carboxylic Acids: Hydrolysis

3.2K
Amides can undergo either acid-catalyzed hydrolysis or base-promoted hydrolysis through a typical nucleophilic acyl substitution. Each hydrolysis requires severe conditions.
Acid-catalyzed hydrolysis:
Hydrolysis of amides under acidic conditions yields carboxylic acids. Since the reaction occurs slowly, hydrolysis requires the conditions of heat.
The mechanism begins with the protonation of the carbonyl oxygen by the acid catalyst. The protonation makes the amide carbonyl carbon more...
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Peptide Boronic Acids by Late-Stage Hydroboration on the Solid Phase.

Marius Werner1,2, Julian Brinkhofer1, Leon Hammermüller1

  • 1Institute of Organic Chemistry, Heidelberg University, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.

Advanced Science (Weinheim, Baden-Wurttemberg, Germany)
|May 29, 2024
PubMed
Summary

New on-resin methods synthesize peptide boronic acids for biomolecule applications. These organoboron compounds offer shorter linkers and versatile applications in drug discovery and diagnostics.

Keywords:
hydroborationlate‐stage functionalizationnonproteinogenic amino acidspeptidessolid‐phase synthesis

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Area of Science:

  • Organic Chemistry
  • Biochemistry
  • Medicinal Chemistry

Background:

  • Organoboron compounds are valuable in diverse research areas.
  • Incorporating boronic acids into biomolecules is a significant synthetic challenge.
  • Existing methods for peptide boronic acid synthesis have limitations.

Purpose of the Study:

  • To develop efficient on-resin chemical syntheses for peptide boronic acids.
  • To create methods for incorporating aliphatic and vinylogous peptide boronic acids into peptides and peptoids.
  • To explore the applications of these novel peptide boronic acids.

Main Methods:

  • Transition metal-catalyzed late-stage hydroboration of alkene and alkyne groups in peptides and peptoids.
  • On-resin synthesis utilizing allyl- and propargylglycine residues.
  • Derivatization via the Petasis reaction and carbohydrate binding studies.

Main Results:

  • Successful synthesis of peptide boronic acids with shorter linkers compared to previous methods.
  • Methods demonstrated regio- and stereoselectivity, compatibility with canonical amino acids, and applicability to various peptide sequences.
  • Demonstrated reversible carbohydrate binding capabilities of the synthesized peptide boronic acids.

Conclusions:

  • The developed methods provide efficient access to peptide boronic acids.
  • These compounds show promise for drug discovery, glycan-specific recognition, controlled release, and diagnostics.
  • The synthesis is versatile and applicable to complex peptide sequences.