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The radical dimerization of ketones or aldehydes gives vicinal diols through a pinacol coupling reaction. However, the behavior of titanium metals used for the reaction as a source of electrons is unusual. When the reaction is carried out in the presence of titanium, diols can be isolated at low temperatures. Else titanium further reacts with diols, forming alkenes through the McMurry reaction.
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Acid Halides to Amides: Aminolysis01:07

Acid Halides to Amides: Aminolysis

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Aminolysis is a nucleophilic acyl substitution reaction, where ammonia or amines act as nucleophiles to give the substitution product. Acid halides react with ammonia, primary amines, and secondary amines to yield primary, secondary, and tertiary amides, respectively.
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Carbonyl compounds and primary amines undergo reductive amination first to produce imines, followed by secondary amines in the same reaction mixture, using selective reducing agents like sodium cyanoborohydride or sodium triacetoxyborohydride. Reductive amination produces different degrees of substitution of amines depending on the starting amine substrate.
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Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
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Cope elimination reaction involves the conversion of tertiary amines to alkene using hydrogen peroxide under thermal conditions, as depicted in figure 1.
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DMAP and PivOH-promoted amination/allenization reaction.

Bo-Sheng Zhang1, Yuke Li, Xue-Ya Gou

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This study introduces a novel palladium-catalyzed reaction for ortho-C-H amination and ipso-allenization of iodobenzenes, utilizing cooperative catalysis with DMAP and PivOH ligands. Mechanistic studies suggest distinct roles for each ligand in the cooperative catalytic cycle.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Organometallic Chemistry

Background:

  • Palladium-catalyzed C-H functionalization is a powerful tool in organic synthesis.
  • Developing cooperative catalytic systems can enhance reaction efficiency and selectivity.
  • Ortho-selective C-H amination and allenylation of aryl halides remain challenging.

Purpose of the Study:

  • To report the first cooperative catalytic system for ortho-C-H amination and ipso-allenization of iodobenzenes.
  • To investigate the mechanistic roles of DMAP, PivOH, and norbornene ligands in the Pd-catalyzed reaction.
  • To establish a new synthetic methodology for accessing complex organic molecules.

Main Methods:

  • Palladium/norbornene cooperative catalysis.
  • Use of 4-Dimethylaminopyridine (DMAP) and Pivalic acid (PivOH) as ligands/promoters.
  • Control experiments to elucidate reaction pathways.
  • Density Functional Theory (DFT) calculations for mechanistic insights.

Main Results:

  • Successful demonstration of the first DMAP and PivOH-promoted ortho-C-H amination and ipso-allenization of iodobenzenes.
  • Identification of cooperative effects between Pd, norbornene, DMAP, and PivOH.
  • Evidence suggesting distinct mechanistic roles and pathways for the three ligands.

Conclusions:

  • The developed Pd/norbornene cooperative catalysis system enables efficient ortho-C-H amination and ipso-allenization of iodobenzenes.
  • Mechanistic investigations provide valuable insights into the cooperative action of the ligands.
  • This work opens new avenues for C-H functionalization strategies.