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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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Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
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Wilhelm Rudolph Fittig discovered the pinacol coupling reaction in 1859. It is a radical dimerization reaction and involves the reductive coupling of aldehydes or ketones in the presence of hydrocarbon solvent to yield vicinal diols.
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The Wittig reaction, which converts aldehydes or ketones to alkenes using phosphorus ylides, proceeds through a nucleophilic addition‒elimination process.
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Introduction
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Nickel-Catalyzed Reductive Csp2-Csp3 Cross Coupling Using Phosphonium Salts.

Huifei Wang1,2,3, Mengwan Yang1, Yuting Wang1

  • 1Key Laboratory of Advanced Mass Spectrometry and Molecular Analysis of Zhejiang Province, School of Material Science and Chemical Engineering, Ningbo University, Ningbo 315211, China.

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|October 19, 2021
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A new nickel-catalyzed reaction enables the direct formation of carbon-carbon bonds using phosphonium salts and allylic electrophiles. This method offers broad compatibility, even with challenging heterocyclic compounds.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Carbon-carbon bond formation is fundamental in organic synthesis.
  • Reductive cross-coupling reactions offer efficient pathways for C-C bond construction.
  • Developing novel catalytic systems for challenging coupling reactions remains an active area of research.

Purpose of the Study:

  • To develop a novel nickel-catalyzed reductive cross-coupling protocol.
  • To enable the direct construction of C(sp2)-C(sp3) bonds.
  • To achieve coupling with phosphonium salts and allylic C(sp3)-O bond electrophiles.

Main Methods:

  • Nickel-catalyzed reductive cross-coupling reaction.
  • Utilized phosphonium salts and allylic C(sp3)-O bond electrophiles as substrates.
  • Investigated reaction conditions for optimal yield and selectivity.

Main Results:

  • Successfully developed a nickel-catalyzed reductive cross-coupling protocol.
  • Demonstrated direct construction of the C(sp2)-C(sp3) bond.
  • Achieved broad substrate scope, high functional-group tolerance, and heterocycle compatibility.
  • First-time accomplishment of reductive cross-coupling with heterocyclic thiazolylphosphonium salts.

Conclusions:

  • The developed protocol provides an efficient method for C(sp2)-C(sp3) bond formation.
  • The reaction exhibits excellent functional group tolerance and compatibility with heterocycles.
  • This work expands the scope of reductive cross-coupling reactions, particularly for challenging heterocyclic substrates.