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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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Preparation of Epoxides03:00

Preparation of Epoxides

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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...
8.0K
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.
8.7K
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

2.3K
Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, β-ketoesters, or β-diketones) and α,β-unsaturated carbonyl acceptors. Named after Sir Robert Robinson, who discovered it, this reaction yields a six-membered ring with three new C–C bonds (two σ bonds and one π bond).
2.3K
Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

8.3K
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...
8.3K
Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

2.2K
Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.
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Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
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Boroxine template for macrocyclization and postfunctionalization.

Kosuke Ono1, Satoru Onodera2, Hidetoshi Kawai2

  • 1School of Science, Tokyo Institute of Technology, O-okayama Meguro-ku, Tokyo 152-8551, Japan. k.ono@chem.titech.ac.jp.

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|October 10, 2022
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Summary
This summary is machine-generated.

A new method uses boroxine formation for synthesizing large macrocyclic molecules. This boroxine-templated macrocyclization simplifies procedures and avoids extra template molecules.

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Area of Science:

  • Organic Chemistry
  • Supramolecular Chemistry
  • Synthetic Chemistry

Background:

  • Macrocyclic compounds are important in various scientific fields.
  • Traditional synthesis of large macrocycles can be challenging and require template molecules.

Purpose of the Study:

  • To develop a novel synthetic strategy for large macrocyclic molecules.
  • To utilize boroxine formation as a covalent template for macrocyclization.

Main Methods:

  • Synthesis of 3,5-bis(alkenyloxy)phenylboroxines via dehydration of boronic acids.
  • Intramolecular olefin metathesis of boroxines with varying alkenyl chain lengths.
  • Use of pinacol for stabilization and modification.

Main Results:

  • Successfully synthesized 39-, 45-, and 51-membered macrocyclic compounds containing three boronate units.
  • Demonstrated the boroxine moiety's function as a covalent template.
  • Showcased the boroxine's utility for postmodification of the macrocycle.

Conclusions:

  • Boroxine-templated macrocyclization offers a simplified and efficient synthetic route.
  • This method eliminates the need for external template molecules.
  • The strategy is versatile for creating diverse large macrocyclic structures.