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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 stereochemistry.

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.

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...

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

If a set of reactants can yield multiple constitutional isomers, but one of the isomers is obtained as the major product, the reaction is said to be regioselective. In such reactions, bond formation or breaking is favored at one reaction site over others.
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...

Radical Anti-Markovnikov Addition to Alkenes: Overview

Radical Anti-Markovnikov Addition to Alkenes: Overview

The addition of hydrogen bromide to alkenes in the presence of hydroperoxides or peroxides proceeds via an anti-Markovnikov pathway and yields alkyl bromides.

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

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Nickel-Catalyzed Boron-Stereogenic Hydroboration.

Siqiang Fang^1,2, Peiqi Zhang², Guanwen Hu²

¹Department of Chemistry, The Chinese University of Hong Kong, Shatin, N.T., Kowloon 999077, Hong Kong SAR China.

Journal of the American Chemical Society

|March 11, 2026

Summary

This summary is machine-generated.

Researchers developed a novel nickel-catalyzed hydroboration reaction. This method creates chiral organoboranes with both boron and carbon stereocenters, advancing asymmetric synthesis.

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Area of Science:

Organic Chemistry
Catalysis
Asymmetric Synthesis

Background:

Hydroboration is crucial for olefin functionalization and organoboron synthesis.
Asymmetric hydroboration typically creates chiral carbon centers, but chiral boron centers remain a challenge.

Purpose of the Study:

To develop a catalytic method for boron-stereogenic hydroboration.
To construct enantioenriched B(sp3)-C(sp3) skeletons with both boron and carbon stereocenters.

Main Methods:

Rational design of a nickel/chiral phosphoramidite catalyst system.
Boron-stereogenic hydroboration of diverse olefins using a prochiral vinylborane reagent.
Experimental and computational studies to elucidate the reaction mechanism.

Main Results:

Successful boron-stereogenic hydroboration of unactivated and activated olefins.
Construction of molecules with both boron and carbon stereocenters.
Identification of a unique ligand-to-ligand hydrogen transfer pathway for B(sp3)-H bond activation.

Conclusions:

The developed protocol provides access to diverse acyclic chiral organoboranes.
The reaction exhibits broad substrate scope and functional group compatibility.
Mechanistic insights into enantioselectivity were gained through computational and experimental studies.