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Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

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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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Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

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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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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

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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.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
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Preparation of Alkynes: Dehydrohalogenation02:34

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Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.
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Preparation of Alkynes: Alkylation Reaction02:27

Preparation of Alkynes: Alkylation Reaction

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Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
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Preparation of Aldehydes and Ketones from Alcohols, Alkenes, and Alkynes01:33

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Aldehydes and ketones are prepared from alcohols, alkenes, and alkynes via different reaction pathways. Alcohols are the most commonly used substrates for synthesizing aldehydes and ketones. The conversion of alcohol to aldehyde, which involves the oxidation process, depends on the class of the alcohol used and the strength of the oxidizing agent. For instance, primary alcohol will form an aldehyde when treated with a weak oxidizing agent; however, it gets over-oxidized to a carboxylic acid in...
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Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine N-Oxide Dehydrate
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Aliphatic C-H Functionalization Using Pyridine N-Oxides as H-Atom Abstraction Agents.

Marcel Schlegel1, Siran Qian1, David A Nicewicz1

  • 1Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, United States.

ACS Catalysis
|September 20, 2023
PubMed
Summary

This study demonstrates visible-light-mediated alkylation and heteroarylation of unactivated C(sp3)-H bonds using acridinium catalysts and pyridine N-oxides. The method efficiently functionalizes diverse aliphatic and heteroaromatic compounds via oxygen-centered radical intermediates.

Keywords:
C–H functionalizationacridiniumalkylationheteroarylationphotoredox catalysispyridine N-oxide

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Area of Science:

  • Organic Chemistry
  • Photocatalysis
  • C-H Functionalization

Background:

  • C(sp3)-H bond functionalization remains a significant challenge in organic synthesis.
  • Developing catalytic methods for direct C-H activation under mild conditions is highly desirable.

Purpose of the Study:

  • To develop a novel method for the alkylation and heteroarylation of unactivated C(sp3)-H bonds.
  • To utilize visible light photocatalysis for efficient C-H functionalization.

Main Methods:

  • Employing an acridinium photoredox catalyst.
  • Using pyridine N-oxides as hydrogen atom transfer (HAT) precursors.
  • Irradiation with visible light.

Main Results:

  • Successful alkylation and heteroarylation of tertiary, secondary, and primary C(sp3)-H bonds.
  • Generation of oxygen-centered radicals as key intermediates.
  • Broad substrate scope, including diverse aliphatic C-H bonds and heteroarenes.

Conclusions:

  • The developed method provides an efficient route for C(sp3)-H functionalization.
  • The use of pyridine N-oxides offers tunable reactivity through structural modifications.
  • This photocatalytic approach broadens the scope of C-H activation strategies.