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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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Properties of Organometallic Compounds01:23

Properties of Organometallic Compounds

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Organometallic compounds are compounds that contain a carbon–metal bond. Carbon belongs to an organyl group like alkyl, aryl, allyl, or benzyl groups. The metal can be from Group I or Group II of the periodic table, a transition metal, or a semimetal.
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Directing Effect of Substituents: meta-Directing Groups01:09

Directing Effect of Substituents: meta-Directing Groups

5.0K
Substituents on the benzene ring that direct an incoming electrophile to undergo substitution at the meta position are called meta directors. All meta directors either have a positive charge on the atom directly bonded to the ring or a partial positive charge. These groups function by withdrawing electrons from the ring through inductive and resonance effects. Consider the carbocation intermediates formed upon the addition of an electrophile on nitrobenzene at the...
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Properties of Transition Metals02:58

Properties of Transition Metals

27.5K
Transition metals are defined as those elements that have partially filled d orbitals. As shown in Figure 1, the d-block elements in groups 3–12 are transition elements. The f-block elements, also called inner transition metals (the lanthanides and actinides), also meet this criterion because the d orbital is partially occupied before the f orbitals.
27.5K
meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H01:13

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All meta-directing substituents are deactivating groups. These substituents withdraw electrons from the aromatic ring, making the ring less reactive toward electrophilic substitution. For example, the nitration of nitrobenzene is 100,000 times slower than that of benzene because of the deactivating effect of the nitro group. The first step in an electrophilic aromatic substitution is the addition of an electrophile to form a resonance-stabilized carbocation. The energy diagrams for...
5.9K
ortho–para-Directing Deactivators: Halogens01:24

ortho–para-Directing Deactivators: Halogens

5.9K
Halogens are ortho–para directors. They are more electronegative than carbon. Therefore, as ring substituents, they can withdraw electrons through the inductive effect and deactivate the aromatic ring towards electrophilic substitution. Halogens also have an electron-donating resonance effect on the ring, which influences the orientation of the incoming electrophile. If an electrophile attacks at the ortho or the para position, the halogen donates electrons and stabilizes the intermediate...
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Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene
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Combining transition metals and transient directing groups for C-H functionalizations.

Trisha Bhattacharya1, Sandeep Pimparkar1,2, Debabrata Maiti1,2

  • 1Department of Chemistry, IIT Bombay Powai Mumbai-400076 India dmaiti@chem.iitb.ac.in.

RSC Advances
|May 11, 2022
PubMed
Summary
This summary is machine-generated.

Transient directing groups (tDGs) offer a more efficient approach to C-H bond activation compared to traditional directing groups (DGs). This study explores the use of tDGs with rhodium, ruthenium, and palladium catalysts for selective chemical transformations.

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Area of Science:

  • Synthetic Chemistry
  • Organometallic Chemistry

Background:

  • C-H bond activation is crucial in synthetic chemistry, with transition metal catalysis being a primary strategy.
  • Directing group (DG) assisted C-H activation offers site selectivity but requires extra synthetic steps for DG installation and removal.
  • This limitation hinders the broader application of DG-based C-H functionalization.

Purpose of the Study:

  • To explore the utility of transient directing groups (tDGs) as a more efficient alternative to traditional DGs.
  • To showcase the application of tDGs in C-H activation reactions catalyzed by second-row transition metals.
  • To provide a comprehensive overview of the advancements in tDG-mediated C-H functionalization.

Main Methods:

  • Utilizing transient directing groups (tDGs) that are installed and removed in situ.
  • Employing prevalent second-row transition metal catalysts, specifically rhodium (Rh), ruthenium (Ru), and palladium (Pd).
  • Investigating site-selective C-H functionalization reactions mediated by these catalytic systems.

Main Results:

  • Demonstrated successful C-H activation and functionalization using tDGs with Rh, Ru, and Pd catalysts.
  • Achieved high product yields and selectivity, comparable to or exceeding traditional DG methods.
  • Showcased the reduced synthetic burden by eliminating the need for separate DG installation and removal steps.

Conclusions:

  • Transient directing groups (tDGs) provide a streamlined and effective strategy for C-H bond activation.
  • The use of tDGs with Rh, Ru, and Pd offers a versatile platform for selective organic synthesis.
  • This approach significantly enhances the practicality and efficiency of C-H functionalization methodologies.