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Related Concept Videos

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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Hydroboration-Oxidation of Alkenes03:08

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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.
10.6K
Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

9.2K
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.
9.2K
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...
7.1K
Preparation of Epoxides03:00

Preparation of Epoxides

8.9K
Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...
8.9K
Radical Formation: Homolysis00:54

Radical Formation: Homolysis

4.1K
A bond is formed between two atoms by sharing two electrons. When this bond is broken by supplying sufficient energy, either two electrons can be taken up by one atom forming ions by the cleavage called heterolysis, or the two electrons are shared by two atoms, with one each creating radicals by the cleavage called homolysis.
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Borylative Heterocyclization without Air-Free Techniques.

Chao Gao1, Shuichi Nakao1, Suzanne A Blum1

  • 1Department of Chemistry, University of California, Irvine, California 92697-2025, United States.

The Journal of Organic Chemistry
|July 17, 2020
PubMed
Summary
This summary is machine-generated.

New borylative heterocyclization methods access useful borylated thiophenes and other compounds without air-free techniques. Catecholboronic esters (Bcat) are stable and directly isolable, expanding their synthetic utility.

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A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
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Area of Science:

  • Organic Chemistry
  • Synthetic Methodology

Background:

  • Traditional borylative heterocyclization often requires stringent air-free conditions.
  • Organoboron compounds, particularly catecholboronic esters (Bcat), can exhibit sensitivity to air and moisture.
  • The stability and isolability of Bcat compounds are crucial for their practical application in synthesis.

Purpose of the Study:

  • To develop practical borylative heterocyclization reactions that do not require air-free techniques.
  • To investigate the stability of Bcat compounds derived from various heterocycles under ambient conditions.
  • To expand the synthetic utility of Bcat compounds through direct isolation and downstream functionalization.

Main Methods:

  • Comparative stability studies of Bcat compounds in air.
  • Development of borylative heterocyclization under ambient-atmosphere conditions using wet solvents.
  • Isolation and characterization of Bcat products.
  • Exploration of downstream functionalization reactions of isolated Bcat products.

Main Results:

  • Successful borylative heterocyclization to form borylated thiophenes, benzothiophenes, and isocoumarins without air-free techniques.
  • Demonstrated that Bcat stability is highly dependent on the heterocycle structure.
  • Identified Bcat products that are chromatography-stable and directly isolable, even with wet solvents.
  • Showcased downstream functionalization of Bcat products, including reactions not feasible with pinacolboronic esters (Bpin).

Conclusions:

  • Borylative heterocyclization can be achieved under practical, ambient-atmosphere conditions.
  • The stability and isolability of Bcat compounds can be controlled by heterocycle structure and reaction conditions.
  • Directly isolable Bcat products offer complementary reactivity to Bpin compounds, expanding organoboron chemistry.