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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.

Regioselectivity and Stereochemistry of Hydroboration

Regioselectivity and Stereochemistry of Hydroboration

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...

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.

Preparation of Alcohols via Addition Reactions

Preparation of Alcohols via Addition Reactions

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...

Free-Radical Chain Reaction and Polymerization of Alkenes

Free-Radical Chain Reaction and Polymerization of Alkenes

The conversion of alkenes to macromolecules called polymers is a reaction of high commercial importance. The structure of the polymer is defined by a repeating unit, while the terminal groups are considered insignificant. The average degree of polymerization represents the number of repeating units in the polymer molecule and is denoted by the subscript n.

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.

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Updated: Aug 18, 2025

Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers

Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers

Published on: December 16, 2022

Converting Commodity Polyolefins to Electronic Materials through Borane-Catalyzed Alkene Isomerization.

Teruhiko Saito^1,2, Megan R Hill¹, Shao-Xiong Lennon Luo¹

¹Department of Chemistry Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139, United States.

Journal of the American Chemical Society

|December 8, 2022

Summary

We developed a catalytic method to convert common polymers into poly(acetylene) (PA)-based multiblock copolymers. These new materials show potential for next-generation electronic devices and even functionalize polyethylene.

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Last Updated: Aug 18, 2025

Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers

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A Simple and Efficient Protocol for the Catalytic Insertion Polymerization of Functional Norbornenes

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Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

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Published on: November 30, 2022

Area of Science:

Polymer Chemistry
Materials Science
Organic Electronics

Background:

Commodity polymers lack functionalization for advanced applications.
Developing new materials for electronics requires novel synthetic strategies.

Purpose of the Study:

To present a catalytic method for polymer functionalization.
To synthesize poly(acetylene) (PA)-based multiblock copolymers from common polymers.
To explore the potential of these materials in electronic devices.

Main Methods:

Catalytic conversion of unsaturated polymers (polybutadiene, polyisoprene, styrene-butadiene copolymers) to PA-based multiblock copolymers.
Demonstration of the method's applicability to polyethylene functionalization.

Main Results:

Achieved conjugation lengths of up to ~20 in PA-based multiblock copolymers.
Successfully converted commodity polymers, including polyethylene, into PA-containing multiblock materials.
Synthesized materials potentially suitable for electronics applications.

Conclusions:

The developed catalytic method offers a novel route for functionalizing commodity polymers.
This approach enables the creation of PA-based multiblock copolymers from widely available plastics.
The resulting materials hold promise for the development of next-generation electronic devices.