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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 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.

Preparation of Alkynes: Alkylation Reaction

Preparation of Alkynes: Alkylation Reaction

Introduction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.

Preparation of Alkynes: Dehydrohalogenation

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Introduction
Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.

Electrophilic Addition to Alkynes: Hydrohalogenation

Electrophilic Addition to Alkynes: Hydrohalogenation

Electrophilic addition of hydrogen halides, HX (X = Cl, Br or I) to alkenes forms alkyl halides as per Markovnikov's rule, where the hydrogen gets added to the less substituted carbon of the double bond. Hydrohalogenation of alkynes takes place in a similar manner, with the first addition of HX forming a vinyl halide and the second giving a geminal dihalide.

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Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry

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Bioorthogonal Hydroamination of Push-Pull-Activated Linear Alkynes.

Dahye Kang^1,2, Sheldon T Cheung^1,2, Justin Kim^1,2

¹Department of Cancer Biology, Dana-Farber Cancer Institute, Boston, MA, 02215, USA.

Angewandte Chemie (International Ed. in English)

|May 21, 2021

Summary

A novel bioorthogonal reaction uses hydroxylamines and activated alkynes for cellular labeling. This uncatalyzed reaction is fast, selective, and stable, offering a new tool for chemical biology.

Keywords:

bioorthogonal enamine N-oxide hydroamination rehybridization effect retro-Cope elimination

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Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes

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Published on: December 16, 2019

Area of Science:

Organic Chemistry
Chemical Biology
Bioorthogonal Chemistry

Background:

Bioorthogonal reactions are crucial for studying biological systems.
Existing methods often face limitations in stability, reactivity, or cellular compatibility.
Developing new bioorthogonal chemistries with improved properties is an ongoing need.

Purpose of the Study:

To describe a new bioorthogonal reaction between N,N-dialkylhydroxylamines and activated halogenated alkynes.
To investigate the use of rehybridization effects for alkyne activation.
To develop a reaction suitable for cellular labeling with high efficiency and selectivity.

Main Methods:

Exploration of rehybridization effects in activating alkynes.
Balancing electronic, stereoelectronic, and inductive factors to achieve alkyne activation.
Utilizing uncatalyzed conjugative retro-Cope elimination reaction.
Assessing reaction kinetics, product regioselectivity, component stability, and cellular compatibility.

Main Results:

A novel bioorthogonal reaction between N,N-dialkylhydroxylamines and activated halogenated alkynes was established.
Electronic effects were shown to sufficiently activate a linear alkyne for reaction while protecting it from cellular nucleophiles.
The reaction proceeds via an uncatalyzed conjugative retro-Cope elimination.
Kinetics comparable to fast strain-promoted azide-alkyne cycloaddition reactions were achieved.
Regioselective product formation, component stability, and suitability for cellular labeling were demonstrated.

Conclusions:

A new, efficient, and selective bioorthogonal reaction has been developed.
This method offers a valuable tool for cellular labeling and chemical biology applications.
The design leverages alkyne rehybridization for controlled reactivity and stability.