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Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

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Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
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Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

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Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
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ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

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

6.1K
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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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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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.
8.4K
Amines to Alkenes: Hofmann Elimination01:16

Amines to Alkenes: Hofmann Elimination

2.5K
Alkenes can be obtained from amines via an E2 elimination. The amine is first converted into a good leaving group, such as a quaternary ammonium salt. This is accomplished by treating the amine with an excess of alkyl halide, which results in a halide salt. Next, the halide salt is transformed into a hydroxide salt that functions as a base to enable elimination.
Under thermal conditions, the hydroxide can abstract a proton from the β carbon; this generates an alkene with the simultaneous...
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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
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Orthogonal Olefination with Organogermanes.

Amit Dahiya1, Markus D Schoetz1, Franziska Schoenebeck1

  • 1Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074, Aachen, Germany.

Angewandte Chemie (International Ed. in English)
|September 12, 2023
PubMed
Summary

A new fully orthogonal olefination reaction enables site- and E-selective coupling of aryl germanes with alkenes. This germanium-based oxidative Heck coupling is fast, operational simple, and tolerates various functional groups.

Keywords:
CatalysisModularityOlefinationOrganogermaneSite-Selectivity

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Area of Science:

  • Organic Chemistry
  • Organometallic Chemistry
  • Synthetic Chemistry

Background:

  • Orthogonal olefination reactions are crucial for constructing complex organic molecules.
  • Existing methods often lack functional group tolerance or require harsh conditions.
  • Development of new catalytic systems is essential for advancing synthetic efficiency.

Purpose of the Study:

  • To report a novel fully orthogonal olefination reaction.
  • To achieve site- and E-selective coupling of aryl germanes with alkenes.
  • To develop a robust catalytic system tolerant of diverse functional groups.

Main Methods:

  • Utilized aryl germanes and alkenes as substrates.
  • Employed a [Ge]-based oxidative Heck coupling strategy.
  • Investigated reaction conditions for optimal site- and E-selectivity.

Main Results:

  • Achieved fully orthogonal olefination with high site- and E-selectivity.
  • Demonstrated tolerance to a wide range of functional groups, including aromatic (pseudo)halogens, silanes, and boronic acid derivatives.
  • Reaction proceeds at room temperature within 10 minutes to 2 hours.
  • The process is base-free and air-tolerant, simplifying operations.

Conclusions:

  • The developed olefination reaction offers a powerful and versatile tool for organic synthesis.
  • The method's broad functional group tolerance and operational simplicity make it highly attractive for various applications.
  • This [Ge]-based oxidative Heck coupling represents a significant advancement in catalytic olefination chemistry.