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Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

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

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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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Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

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In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
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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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Leaving Groups02:14

Leaving Groups

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The nature of leaving groups strongly influences the outcome of a nucleophilic substitution reaction.
In general, in a nucleophilic substitution reaction, a nucleophile displaces a functional group, called the leaving group, from the substrate to give a substituted product. A leaving group departs the substrate molecule through heterolytic cleavage, taking the pair of electrons with it to become a relatively stable weak base in the form of an anion or a neutral molecule.  
In a...
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Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

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Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
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Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
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A traceless directing group for C-H borylation.

Sean M Preshlock1, Donald L Plattner, Peter E Maligres

  • 1Department of Chemistry, Michigan State University, 578 S Shaw Lane, East Lansing, MI 48824-1322 (USA).

Angewandte Chemie (International Ed. in English)
|November 14, 2013
PubMed
Summary

Researchers developed a traceless directing group for C-H borylation reactions. This new method using nitrogen heterocycles and anilines offers higher yields and simplifies processes compared to traditional protection methods.

Keywords:
CH activationanilinesborylationcatalysisnitrogen heterocycles

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Directing groups are crucial for regioselective C-H functionalization.
  • Traditional protecting groups like tert-butoxycarbonyl (Boc) can be cumbersome and require extra steps.
  • Catalytic C-H borylation is a powerful tool for introducing boron functional groups.

Purpose of the Study:

  • To develop a novel, traceless directing group for catalytic C-H borylation.
  • To achieve selectivities comparable to or better than existing methods.
  • To enable in-situ installation and removal of the directing group.

Main Methods:

  • Borylation of nitrogen atoms in nitrogen heterocycles and anilines to form NBpin (N-borylpinacolato) directing groups.
  • Subsequent catalytic C-H borylation reactions guided by the NBpin group.
  • In-situ installation and removal protocols for the NBpin group.

Main Results:

  • The NBpin group serves as an effective traceless directing group for C-H borylation.
  • High regioselectivities were achieved, matching or exceeding those obtained with Boc protection.
  • The NBpin group can be installed and removed efficiently in situ.
  • Substantially higher product yields were observed compared to methods using traditional protecting groups.

Conclusions:

  • Borylation of nitrogen provides a versatile and traceless directing strategy for C-H functionalization.
  • This approach offers a more efficient and higher-yielding alternative to conventional protecting group strategies in catalytic borylation.
  • The in-situ nature of the NBpin group simplifies synthetic routes and enhances overall process efficiency.