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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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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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In the presence of organic peroxides, the addition of hydrogen bromide to an alkene yields the isomer that is not predicted by Markovnikov’s rule. For example, the addition of hydrogen bromide to 2-methylpropene in the presence of peroxides gives 1-bromo-2-methylpropane. This addition reaction proceeds via a free radical mechanism, which reverses the regioselectivity. The free radical reaction mechanism involves three stages: initiation, propagation, and termination.
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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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Regio- and Stereoselective Functionalization Enabled by Bidentate Directing Groups.

Jinwon Jeon1,2, Changseok Lee1,2, Inyoung Park1,2

  • 1Center for Catalytic Hydrocarbon Functionalizations, Institute for Basic Science (IBS), Daejeon, 34141, Republic of Korea.

Chemical Record (New York, N.Y.)
|June 4, 2021
PubMed
Summary

Bidentate directing groups enable precise control over C-H bond and alkene functionalization using transition-metal catalysis. This approach overcomes regiocontrol challenges, offering versatile synthetic strategies for complex molecule synthesis.

Keywords:
C−H functionalizationbidentate directing groupchiral auxiliaryregioselectivitystereoselectivity

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Regiocontrol in C-H bond and alkene functionalization remains a significant challenge in organic synthesis.
  • Bidentate directing groups offer a strategy to guide catalysts to specific reaction sites.
  • Transition-metal catalysis is crucial for developing efficient functionalization reactions.

Purpose of the Study:

  • To highlight recent advancements in regio- and stereocontrolled functionalizations using bidentate directing groups.
  • To showcase the application of transition-metal catalysis in conjunction with bidentate directing groups.
  • To elucidate the mechanistic origins of selectivity through computational studies.

Main Methods:

  • Development of transition-metal catalyzed reactions for alkene functionalization.
  • Design and application of chiral bidentate directing groups for asymmetric C-H functionalization.
  • Density functional theory (DFT) calculations to understand selectivity.

Main Results:

  • Achieved regioselective alkene functionalization guided by bidentate directing groups.
  • Demonstrated asymmetric C-H functionalization using chiral bidentate directing groups.
  • DFT studies provided insights into the origins of regio- and stereoselectivity.

Conclusions:

  • Bidentate directing groups are effective tools for achieving high regio- and stereocontrol in transition-metal catalyzed reactions.
  • This methodology provides versatile pathways for synthesizing complex organic molecules.
  • Computational studies are valuable for understanding and optimizing catalytic systems.