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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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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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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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This lesson delves into the concept of protection and deprotection of a functional group fundamental to synthetic organic chemistry. These phenomena are explained in the context of aliphatic and aromatic alcohols.
Protection
It defines a protecting group as the masking agent to make the more reactive species inert to a given set of conditions. This concept is depicted via the illustration of liquid flow through different outlets in an assembly of pipes. The analogy helps to understand the role...
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If a set of reactants can yield multiple constitutional isomers, but one of the isomers is obtained as the major product, the reaction is said to be regioselective. In such reactions, bond formation or breaking is favored at one reaction site over others.
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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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Sterically Congested Protecting Group for a Boronyl Group in Iterative Aminations.

Takaki Nojiri1, Naoki Tsuchiya1, Takashi Nishikata1

  • 1Graduate School of Science and Engineering, Yamaguchi University, 2-16-1 Tokiwadai, Ube, Yamaguchi, 755-8611, Japan.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|January 21, 2024
PubMed
Summary

A novel α-hydroxycarboxamide protecting group stabilizes boron reagents for controlled amination reactions. This method enables precise synthesis of multi-arylamino substituted arenes via Chan-Evans-Lam or Buchwald-Hartwig amination.

Keywords:
AminationBoron compoundOxazaborolidinoneProtecting

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Area of Science:

  • Organic Chemistry
  • Synthetic Methodology
  • Boron Chemistry

Background:

  • Boron reagents are versatile in organic synthesis.
  • Protecting group strategies are crucial for controlling reactivity.
  • Amination reactions are key for constructing C-N bonds.

Purpose of the Study:

  • To develop a robust protecting group for boron reagents.
  • To enable controlled amination of arylboron compounds.
  • To achieve precise synthesis of poly-arylamino arenes.

Main Methods:

  • Condensation of α-hydroxycarboxamide with arylboronic acid to form aryloxazaborolidinone (ArOxB).
  • Utilizing Chan-Evans-Lam (C-E-L) or Buchwald-Hartwig (B-H) amination conditions.
  • Employing Cu(II) catalysis for direct C-E-L amination in oxidative atmospheres.

Main Results:

  • The α-hydroxycarboxamide moiety effectively protects the boronyl group.
  • Reactivity of the C-B bond in ArOxB is tunable via steric and electronic effects.
  • Successful amination reactions (C-E-L and B-H) were achieved while preserving the C-B bond.
  • Direct C-E-L amination of ArOxB was demonstrated using Cu(II) activation.

Conclusions:

  • The developed aryloxazaborolidinone (ArOxB) framework offers controlled reactivity for boron reagents.
  • This methodology provides a precise route for synthesizing complex arylamino substituted arenes.
  • The protecting group strategy is compatible with established amination protocols and offers new activation pathways.