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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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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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Regioselectivity and Stereochemistry of Hydroboration02:36

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A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
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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Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

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Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
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Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

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Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
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Electrophilic Addition to Alkynes: Hydrohalogenation02:35

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Electrophilic addition of hydrogen halides, HX (X = Cl, Br or I) to alkenes forms alkyl halides as per Markovnikov's rule, where the hydrogen gets added to the less substituted carbon of the double bond. Hydrohalogenation of alkynes takes place in a similar manner, with the first addition of HX forming a vinyl halide and the second giving a geminal dihalide.
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Updated: Apr 29, 2026

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
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Gold-catalyzed C(sp3)-H bond functionalization.

Jin Xie1, Changduo Pan, Ablimit Abdukader

  • 1State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, China. cjzhu@nju.edu.cn.

Chemical Society Reviews
|May 24, 2014
PubMed
Summary
This summary is machine-generated.

Gold catalysis efficiently functionalizes challenging Csp(3)-H bonds, enabling new synthetic routes. This review covers recent advances in gold-catalyzed oxidative and redox-neutral Csp(3)-H bond activation for sustainable chemical synthesis.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Carbon-hydrogen (C-H) bonds are fundamental in organic chemistry.
  • Gold catalysis has advanced unsaturated C-H bond functionalization.
  • Selective cleavage of Csp(3)-H bonds remains a significant synthetic challenge due to their high dissociation energy and low acidity.

Purpose of the Study:

  • To review recent progress in gold-catalyzed Csp(3)-H bond functionalization.
  • To highlight methods for the selective cleavage of Csp(3)-H bonds.
  • To showcase applications in the sustainable synthesis of fine chemicals.

Main Methods:

  • Focus on gold-catalyzed oxidative Csp(3)-H functionalization.
  • Discuss gold-catalyzed redox-neutral Csp(3)-H functionalization.
  • Review the formation of new carbon-carbon and carbon-heteroatom bonds.

Main Results:

  • Demonstration of efficient and selective gold-catalyzed Csp(3)-H bond cleavage.
  • Advancement of synthetic strategies for complex molecule construction.
  • Development of economical and sustainable chemical processes.

Conclusions:

  • Gold catalysis offers powerful solutions for challenging Csp(3)-H bond functionalization.
  • These methods provide new avenues for sustainable synthesis.
  • The field is rapidly evolving with significant potential for fine chemical production.