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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

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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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Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

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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.
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation reactions,...
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Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

8.9K
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.
8.9K
Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule02:17

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

16.2K
If a set of reactants can yield multiple constitutional isomers, but one of the isomers is obtained as the major product, the reaction is said to be regioselective. In such reactions, bond formation or breaking is favored at one reaction site over others.
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...
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Reduction of Alkenes: Catalytic Hydrogenation02:13

Reduction of Alkenes: Catalytic Hydrogenation

13.9K
Alkenes undergo reduction by the addition of molecular hydrogen to give alkanes. Because the process generally occurs in the presence of a transition-metal catalyst, the reaction is called catalytic hydrogenation.
Metals like palladium, platinum, and nickel are commonly used in their solid forms — fine powder on an inert surface. As these catalysts remain insoluble in the reaction mixture, they are referred to as heterogeneous catalysts.
The hydrogenation process takes place on the...
13.9K
Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

9.4K
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 stereochemistry.
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Modular Iminophosphorane as Hydrogen Atom Transfer Catalyst for Selective C(sp3)-H Functionalization.

Min Jiang1, Wei Zhang1, Pu-Sheng Wang1

  • 1Hefei National Research Center for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, P. R. China.

Organic Letters
|October 6, 2025
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Iminophosphoranes act as tunable hydrogen atom transfer catalysts, overriding typical C(sp3)-H bond preferences. Acridinium photoredox catalysis enables selective C(sp3)-H alkylation, with substituent modulation enhancing regioselectivity.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Photoredox Catalysis

Background:

  • Iminophosphoranes are versatile compounds synthesized through the Staudinger reaction.
  • Hydrogen atom transfer (HAT) catalysis offers a powerful method for C-H functionalization.
  • Controlling regioselectivity in C-H activation remains a significant challenge in organic synthesis.

Purpose of the Study:

  • To develop iminophosphoranes as tunable hydrogen atom transfer catalysts.
  • To achieve selective C(sp3)-H alkylation of diverse substrates using photoredox catalysis.
  • To enhance regioselectivity by modulating iminophosphorane substituents.

Main Methods:

  • Synthesis of iminophosphoranes via the Staudinger reaction.
  • Application of acridinium photoredox catalysis for C(sp3)-H alkylation.
  • Systematic variation of phosphorus and nitrogen substituents on the iminophosphorane scaffold.

Main Results:

  • Iminophosphorane catalysts successfully mediated hydrogen atom transfer, overriding thermodynamic C(sp3)-H bond-strength preferences.
  • Selective C(sp3)-H alkylation was achieved across a range of substrates under acridinium photoredox catalysis.
  • Modulation of catalyst substituents allowed for tunable enhancement of regioselectivity, favoring sterically accessible positions.

Conclusions:

  • Iminophosphoranes are effective tunable HAT catalysts for C(sp3)-H functionalization.
  • Acridinium photoredox catalysis provides a platform for selective C(sp3)-H alkylation using these catalysts.
  • Catalyst design through substituent modulation offers precise control over reaction regioselectivity.