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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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In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.
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Baeyer–Villiger oxidation converts aldehydes to carboxylic acids and ketones to esters. The reaction uses peroxy acids or peracids and is often catalyzed by acid. The reaction is named after its pioneers, Adolf von Baeyer and Victor Villiger. The reaction is achieved by a wide range of peracids such as m-chloroperoxybenzoic acid (mCPBA), perbenzoic acid (C6H5COOOH), peracetic acid (CH3COOOH), hydrogen peroxide (H2O2), and tert-butyl hydroperoxide (t-BuOOH).
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Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
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Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
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The Hofmann and Curtius rearrangement reactions can be applied to synthesize primary amines from carboxylic acid derivatives such as amides and acyl azides. In the Hofmann rearrangement, a primary amide undergoes deprotonation in the presence of a base, followed by halogenation to generate an N-haloamide. A second proton abstraction produces a stabilized anionic species, which rearranges to an isocyanate intermediate via an alkyl group migration from the carbonyl carbon to the neighboring...
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Updated: Sep 17, 2025

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Dual 1,2-Migration-Enabled β-Boryl Amide Synthesis.

Qi Cheng1, Hanlin Yang1, Shunle Hu1

  • 1Institute of Frontier Chemistry, School of Chemistry and Chemical Engineering, Shandong University, Qingdao, 266237, China.

Organic Letters
|July 2, 2025
PubMed
Summary
This summary is machine-generated.

A new metal-free method synthesizes multisubstituted β-boryl amides using dioxazolones and vinyl boronate complexes. This approach efficiently creates diverse amides with borylated quaternary centers, useful for further chemical transformations.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Medicinal Chemistry

Background:

  • Metal-free synthetic strategies are highly sought after in organic chemistry.
  • Developing efficient routes to complex organic molecules like β-boryl amides is crucial for drug discovery and materials science.

Purpose of the Study:

  • To develop a novel, metal-free synthetic route for multisubstituted β-boryl amides.
  • To explore the utility of dioxazolones and vinyl boronate complexes in constructing complex organic structures.
  • To demonstrate the synthetic versatility of the newly developed protocol.

Main Methods:

  • Coupling of dioxazolones with vinyl boronate complexes.
  • Utilizing a Curtius-type rearrangement of dioxazolones to generate isocyanates in situ.
  • Characterization of the synthesized β-boryl amides and their downstream transformations.

Main Results:

  • Successful synthesis of multisubstituted β-boryl amides via a metal-free pathway.
  • Efficient construction of structurally diverse β-boryl amides containing a borylated quaternary carbon center.
  • Demonstration of the broad synthetic utility through subsequent modifications of the boron and carbonyl groups.

Conclusions:

  • The developed protocol offers a novel and efficient metal-free method for synthesizing β-boryl amides.
  • This approach provides access to valuable borylated compounds with potential applications in various chemical fields.
  • The synthetic flexibility of the method allows for further derivatization, expanding its utility.