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Related Concept Videos

Acid Halides to Ketones: Gilman Reagent01:14

Acid Halides to Ketones: Gilman Reagent

Lithium dialkyl cuprate, also known as Gilman reagents, selectively reduces acid halides to ketones. The acid chloride is treated with Gilman reagent at −78 °C in the presence of ether solution to produce a ketone in good yield.
As shown below, the mechanism proceeds in two steps. First, one of the alkyl groups of the reagent acts as a nucleophile and attacks the acyl carbon of the acid chloride to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen double...
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Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
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Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
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In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic halogen to form a...
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Copper catalyzed C-H functionalization for direct Mannich reactions.

Magnus Rueping1, Nikita Tolstoluzhsky

  • 1Institute of Organic Chemistry, RWTH Aachen University, Aachen, Germany. Magnus.Rueping@rwth-aachen.de

Organic Letters
|February 4, 2011
PubMed
Summary
This summary is machine-generated.

A new method enables direct addition of alkyl azaarenes to N-sulfonyl aldimines. Copper catalysts facilitate Mannich-type reactions, offering a mild and fast route to functionalized heterocycles.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Heterocyclic Chemistry

Background:

  • N-sulfonyl aldimines are versatile synthetic intermediates.
  • Functionalized heterocycles are important structural motifs in pharmaceuticals and materials.
  • Direct C-H functionalization strategies are highly desirable for efficient synthesis.

Purpose of the Study:

  • To develop a practical and direct protocol for the addition of α- and γ-alkyl azaarenes to N-sulfonyl aldimines.
  • To explore the use of copper salts as efficient Lewis acid catalysts for this transformation.
  • To provide a mild and fast access to various functionalized heterocycles.

Main Methods:

  • Direct addition reaction between α- and γ-alkyl azaarenes and N-sulfonyl aldimines.
  • Utilized copper salts as Lewis acid catalysts.
  • Employed mild reaction conditions and short reaction times.

Main Results:

  • Successfully developed a protocol for the direct addition of α- and γ-alkyl azaarenes to N-sulfonyl aldimines.
  • Demonstrated the efficiency of copper salts as Lewis acid catalysts.
  • Achieved a mild and fast synthesis of various functionalized heterocycles.

Conclusions:

  • A practical and direct Mannich-type reaction protocol has been established.
  • Copper-catalyzed addition offers an efficient route to functionalized heterocycles.
  • This method provides a valuable tool for the synthesis of complex organic molecules.