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

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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

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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...
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Organic Compounds03:02

Organic Compounds

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All living things are formed mostly of carbon compounds called organic compounds. The category of organic compounds includes both natural and synthetic compounds that contain carbon. Although a single, precise definition has yet to be identified by the chemistry community, most agree that a defining trait of organic molecules is the presence of carbon as the principal element, bonded to hydrogen and other carbon atoms. However, some carbon-containing compounds such as carbonates, cyanides, and...
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Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

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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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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: Alkylation Reaction02:27

Preparation of Alkynes: Alkylation Reaction

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Introduction
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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Large-Scale Selective Functionalization of Alkanes.

Karen I Goldberg1, Alan S Goldman2

  • 1Department of Chemistry, University of Washington , Box 351700, Seattle, Washington 98195, United States.

Accounts of Chemical Research
|September 26, 2017
PubMed
Summary
This summary is machine-generated.

Developing selective alkane functionalization requires highly active, long-lived catalysts and atom-economical processes. Current research explores molecular transition metal catalysts for efficient and sustainable C-H bond transformations.

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Area of Science:

  • Catalysis
  • Organic Chemistry
  • Sustainable Chemistry

Background:

  • Significant advancements in C-H bond functionalization have been achieved over decades.
  • Commercial-scale selective alkane functionalization remains a major challenge.
  • Existing methods often lack the required activity, selectivity, or atom economy for industrial application.

Purpose of the Study:

  • To review progress and promising leads in developing catalysts for selective alkane functionalization.
  • To highlight the requirements for commercially viable large-scale alkane conversion processes.
  • To focus on systems utilizing molecular transition metal catalysts.

Main Methods:

  • Review of recent literature on C-H bond functionalization.
  • Analysis of catalytic systems, particularly those involving transition metals.
  • Evaluation of catalyst performance based on activity, selectivity, and longevity.
  • Assessment of atom economy and byproduct profiles.

Main Results:

  • Progress has been made in developing catalysts for C-H bond functionalization.
  • Challenges remain in achieving high selectivity and long catalyst lifetimes for alkanes.
  • Molecular transition metal catalysts show promise for future applications.
  • The need for atom-economical processes with benign or valuable byproducts is emphasized.

Conclusions:

  • Highly active, selective, and long-lived catalysts are essential for large-scale alkane functionalization.
  • Atom economy and benign byproduct formation are critical for sustainable processes.
  • Molecular transition metal catalysis offers promising avenues for achieving these goals.