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Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.

Hydroboration-Oxidation of Alkenes

Hydroboration-Oxidation of Alkenes

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.

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

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.

Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration

Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration

Introduction
Analogous to alkenes, alkynes also undergo acid-catalyzed hydration. While the addition of water to an alkene gives an alcohol, hydration of alkynes produces different products such as aldehydes and ketones.

Reduction of Alkenes: Catalytic Hydrogenation

Reduction of Alkenes: Catalytic Hydrogenation

Alkenes undergo reduction by the addition of molecular hydrogen to give alkanes. Because the process generally occurs in the presence of a transition-metal catalyst, the reaction is called catalytic hydrogenation.
Metals like palladium, platinum, and nickel are commonly used in their solid forms — fine powder on an inert surface. As these catalysts remain insoluble in the reaction mixture, they are referred to as heterogeneous catalysts.
The hydrogenation process takes place on the...

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...

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Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes

Published on: September 8, 2013

Iron-Catalyzed Alkene Hydroalumination.

Wen-Tao Li¹, Qiao Zhang¹, Meng-Yang Hu¹

¹Frontiers Science Center of Organic Matters, The State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China.

Organic Letters

|July 24, 2023

Summary

This summary is machine-generated.

This study introduces a novel iron-catalyzed Markovnikov hydroalumination of aromatic alkenes, yielding unique benzylaluminum complexes. This method offers a new regioselectivity pathway distinct from traditional anti-Markovnikov additions in olefin chemistry.

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Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

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Published on: June 21, 2017

Area of Science:

Organometallic Chemistry
Catalysis
Organic Synthesis

Background:

Traditional hydroalumination of olefins typically results in anti-Markovnikov addition.
Achieving Markovnikov selectivity in hydroalumination reactions remains a synthetic challenge.

Purpose of the Study:

To develop a novel catalytic system for Markovnikov hydroalumination of aromatic terminal alkenes.
To synthesize new benzylaluminum complexes.
To investigate the regioselectivity of iron-catalyzed alkene hydroalumination.

Main Methods:

Utilized a well-defined 2,9-diaryl-1,10-phenanthroline modified iron complex as a catalyst.
Employed diisobutylaluminum hydride (DIBAL-H) as the aluminum hydride reagent.
Applied the reaction to aromatic terminal alkenes.

Main Results:

Achieved highly Markovnikov regioselective hydroalumination of aromatic terminal alkenes.
Successfully prepared various new benzylaluminum complexes.
Demonstrated the first instance of iron-catalyzed alkene hydroalumination.
Observed regioselectivity distinct from previously reported hydroalumination reactions.

Conclusions:

The developed iron-catalyzed method provides a new route to Markovnikov hydroalumination products.
This work expands the scope of catalytic alkene functionalization.
The novel regioselectivity offers opportunities for designing new synthetic strategies.