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Related Concept Videos

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration02:34

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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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ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

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All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
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The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
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Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

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The radical dimerization of ketones or aldehydes gives vicinal diols through a pinacol coupling reaction. However, the behavior of titanium metals used for the reaction as a source of electrons is unusual. When the reaction is carried out in the presence of titanium, diols can be isolated at low temperatures. Else titanium further reacts with diols, forming alkenes through the McMurry reaction.
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Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
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Tridentate Directing Groups Stabilize 6-Membered Palladacycles in Catalytic Alkene Hydrofunctionalization.

Miriam L O'Duill1, Rei Matsuura1, Yanyan Wang2

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|October 4, 2017
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New directing groups stabilize key intermediates for remote hydrocarbofunctionalization of alkenes. This palladium-catalyzed reaction offers regioselective control, enabling diverse synthetic applications with tunable outcomes.

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Area of Science:

  • Organic Chemistry
  • Organometallic Chemistry
  • Catalysis

Background:

  • Stabilizing reactive intermediates is crucial for catalytic efficiency.
  • Pincer ligands are known for their robust coordination and stabilization capabilities.
  • Remote functionalization of alkenes presents synthetic challenges due to regioselectivity and kinetic barriers.

Purpose of the Study:

  • To design and synthesize novel removable tridentate directing groups.
  • To enable regioselective remote hydrocarbofunctionalization of various alkene substrates using Pd(II) catalysis.
  • To achieve regiodivergent functionalization of 3-butenoic acid derivatives.

Main Methods:

  • Design and application of removable tridentate directing groups.
  • Palladium(II)-catalyzed hydrocarbofunctionalization reactions.
  • Utilizing substrates like 4-pentenoic acids, allylic alcohols, and homoallyl amines.
  • Mechanistic studies including preliminary computational analysis.

Main Results:

  • Successful stabilization of 6-membered alkyl palladacycle intermediates.
  • Regioselective remote hydrocarbofunctionalization of diverse alkene classes.
  • Demonstration of regiodivergent functionalization of 3-butenoic acid derivatives, yielding Markovnikov or anti-Markovnikov products.
  • Support for the proposed catalytic cycle through mechanistic and computational data.

Conclusions:

  • Removable directing groups offer a powerful strategy for stabilizing challenging intermediates in catalysis.
  • This approach facilitates regioselective and regiodivergent remote hydrocarbofunctionalization of alkenes.
  • The developed methodology expands the synthetic utility of palladium catalysis for complex molecule synthesis.