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Related Concept Videos

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

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.
Carbocations02:10

Carbocations

Carbocations are one of the reaction intermediates formed during several nucleophilic substitutions or elimination reactions. A carbocation is an electron-deficient species with the central carbon atom having six electrons and three bonded atoms. The central carbon in a carbocation is sp2 hybridized with trigonal planar geometry. It has an empty p orbital perpendicular to the plane of the structure that can accept electrons. Thus, carbocations act as strong electrophiles and may react with any...
Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation01:28

Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation

Unlike the easy catalytic hydrogenation of an alkene double bond, hydrogenation of a benzene double bond under similar reaction conditions does not take place easily. For example, in the reduction of stilbene, the benzene ring remains unaffected while the alkene bond gets reduced. Hydrogenation of an alkene double bond is exothermic and a favorable process. In contrast, to hydrogenate the first unsaturated bond of benzene, an energy input is needed; that is, the process is endothermic. This is...
Regioselectivity and Stereochemistry of Hydroboration02:36

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 stereochemistry.
Hydroboration-Oxidation of Alkenes03:08

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.
Reduction of Alkenes: Catalytic Hydrogenation02:13

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 surface of...

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Updated: Jun 8, 2026

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
07:36

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Published on: November 9, 2019

Catalytic carboborations.

Michinori Suginome1

  • 1Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto 615-8510, Japan. suginome@sbchem.kyoto-u.ac.jp

Chemical Record (New York, N.Y.)
|September 18, 2010
PubMed
Summary

Transition-metal-catalyzed carboborations introduce organic and boryl groups to unsaturated molecules. This review covers direct and transmetalative carboboration methods, detailing their mechanisms and applications in organic synthesis.

Area of Science:

  • Organic Chemistry
  • Organometallic Chemistry
  • Catalysis

Background:

  • Carboboration reactions are crucial for synthesizing functionalized organic molecules.
  • Transition-metal catalysis enables efficient and selective carboboration processes.
  • Existing methods involve activation of B-C or B-Cl bonds.

Purpose of the Study:

  • To provide a comprehensive overview of transition-metal-catalyzed carboboration reactions.
  • To discuss the mechanisms of direct and transmetalative carboboration.
  • To present representative results and mechanistic insights.

Main Methods:

  • Overview of direct carboboration via cyanoboranes and alkynylboranes.
  • Review of transmetalative carboboration using organotin and organozirconium reagents.

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Preparation and Use of Carbonyl-decorated Carbenes in the Activation of White Phosphorus

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  • Analysis of mechanistic pathways and catalytic cycles.

    • Main Results:

    • Demonstration of concomitant introduction of organic and boryl groups.
    • Elucidation of distinct mechanisms for direct and transmetalative carboboration.
    • Highlighting the versatility of transition-metal catalysts in these transformations.

    Conclusions:

    • Transition-metal-catalyzed carboborations offer powerful synthetic strategies.
    • Understanding the mechanisms is key to developing new carboboration reactions.
    • These methods provide access to valuable borylated organic compounds.