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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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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 stereochemistry.
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Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

20.4K
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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Preparation of Alcohols via Addition Reactions02:15

Preparation of Alcohols via Addition Reactions

7.1K
Overview
The acid-catalyzed addition of water to the double bond of alkenes is a large-scale industrial method used to synthesize low-molecular-weight alcohols. An acidic atmosphere is required to allow the hydrogen in the water molecule to act as an electrophile and attack the double bond in an alkene. The addition of a proton to the double bond creates a carbocation intermediate. The proton preferentially bonds to the less substituted end of the double bond to create a more stable carbocation...
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Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

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Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...
4.9K
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

7.2K
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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Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
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Boron-mediated directed aromatic C-H hydroxylation.

Jiahang Lv1,2, Binlin Zhao1, Yu Yuan2

  • 1State Key Laboratory of Coordination Chemistry, Chemistry and Biomedicine Innovation Center (ChemBIC), School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, China.

Nature Communications
|March 14, 2020
PubMed
Summary
This summary is machine-generated.

This study introduces a new, mild, and transition metal-free method for C-H hydroxylation of aromatic compounds. The boron-mediated approach enables selective alcohol and phenol synthesis, even with complex molecules.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Catalysis

Background:

  • Transition metal-catalyzed C-H hydroxylation is crucial for synthesizing alcohols and phenols.
  • Achieving site-selective hydroxylation of aromatic C-H bonds under mild conditions, especially in functionalized (hetero)arenes, remains a significant challenge.

Purpose of the Study:

  • To develop a general, mild, and transition metal-free method for C-H hydroxylation of (hetero)arenes.
  • To demonstrate the utility of boron species in mediating this transformation.
  • To achieve ortho C-H hydroxylation with broad functional group compatibility.

Main Methods:

  • Chelation-assisted C-H hydroxylation using boron species.
  • Employing amide directing groups on diverse (hetero)arenes.
  • Utilizing mild reaction conditions.

Main Results:

  • A novel transition metal-free C-H hydroxylation strategy was established.
  • The method demonstrated broad functional group tolerance and applicability to diverse (hetero)arenes.
  • The approach was successfully extended to the synthesis of C7 and C4-hydroxylated indoles.
  • Formal synthesis of phenol intermediates for bioactive molecules was achieved.

Conclusions:

  • The developed boron-mediated C-H hydroxylation offers a mild, efficient, and metal-free alternative for synthesizing functionalized alcohols and phenols.
  • This strategy provides a valuable tool for organic synthesis, particularly for complex molecules and bioactive compound precursors.