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Related Concept Videos

Directing Effect of Substituents: ortho–para-Directing Groups01:14

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Ortho–para directors are substituent groups attached to the benzene ring and direct the addition of an electrophile to the positions ortho or para to the substituent. All electron-donating groups are considered ortho–para directors. They donate electrons to the ring and make the ring more electron-rich. The ring is therefore susceptible to the addition of electrophiles. Substituents such as amino, hydroxy, or alkoxy, containing lone pairs on the atom adjacent to the ring, donate...
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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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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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During the electron transport chain, electrons from NADH and FADH2 are first transferred to complexes I and II, respectively. These two complexes then transfer the electrons to ubiquinol, which carries them further to complex III. Complex III passes the electrons across the intermembrane space to Cyt c, which carries them further to complex IV. Complex IV donates electrons to oxygen and reduces it to water. As electrons pass through complexes I, III, and IV, the energy released aids the pumping...
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A type of Lewis acid-base chemistry involves the formation of a complex ion (or a coordination complex) comprising a central atom, typically a transition metal cation, surrounded by ions or molecules called ligands. These ligands can be neutral molecules like H2O or NH3, or ions such as CN− or OH−. Often, the ligands act as Lewis bases, donating a pair of electrons to the central atom. These types of Lewis acid-base reactions are examples of a broad subdiscipline called coordination...
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Directed ortho C-H borylation catalyzed using Cp*Rh(iii)-NHC complexes.

Jompol Thongpaen1, Thibault E Schmid, Loic Toupet

  • 1Univ Rennes, Ecole Nationale Supérieure de Chimie de Rennes, CNRS, ISCR - UMR 6226, F-35000 Rennes, France. Olivier.basle@ensc-rennes.fr.

Chemical Communications (Cambridge, England)
|July 6, 2018
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Summary

New rhodium(iii) complexes featuring bulky chiral ligands were synthesized. These catalysts show high selectivity for pyridine-directed C-H borylation of arenes under mild conditions.

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Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Organic Synthesis

Background:

  • Transition metal complexes are crucial catalysts in organic synthesis.
  • Rhodium complexes, particularly rhodium(iii), are widely explored for C-H activation reactions.
  • Development of chiral ligands is key for enantioselective catalysis.

Purpose of the Study:

  • To synthesize novel Cp*Rh(NHC) complexes with bulky chiral bidentate NHC-carboxylate ligands.
  • To investigate the catalytic activity of these rhodium(iii) complexes in C-H borylation reactions.
  • To evaluate the selectivity and efficiency of the developed catalytic system.

Main Methods:

  • Efficient synthesis of Cp*Rh(NHC) complexes.
  • Full characterization, including solid-state structural analysis.
  • Application of the complexes as catalysts in pyridine-directed ortho-C-H borylation of arenes.

Main Results:

  • Successful synthesis and full characterization of unprecedented rhodium(iii) complexes.
  • Demonstration of high selectivity in pyridine-directed ortho-C-H borylation.
  • Catalysis achieved under mild reaction conditions.

Conclusions:

  • The novel Cp*Rh(NHC) complexes with bulky chiral ligands are effective catalysts.
  • These complexes offer a highly selective route for ortho-C-H borylation of arenes.
  • The findings contribute to the advancement of catalytic C-H functionalization methodologies.