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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 stereochemistry.

Hybridization of Atomic Orbitals I

Hybridization of Atomic Orbitals I

The mathematical expression known as the wave function, ψ, contains information about each orbital and the wavelike properties of electrons in an isolated atom. When atoms are bound together in a molecule, the wave functions combine to produce new mathematical descriptions that have different shapes. This process of combining the wave functions for atomic orbitals is called hybridization and is mathematically accomplished by the linear combination of atomic orbitals. The new orbitals that...

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.

[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement

[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement

The Cope rearrangement is classified as a [3,3] sigmatropic shift in 1,5-dienes, leading to a more stable, isomeric 1,5-diene. The reaction involves a concerted movement of six electrons, four from two π bonds and two from a σ bond, via an energetically favorable chair-like transition state.

Hybridization of Atomic Orbitals II

Hybridization of Atomic Orbitals II

sp3d and sp3d 2 Hybridization

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

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Tetracoordinate Boron Intermediates Enable Unconventional Transformations.

Kai Yang¹, Qiuling Song^1,2

¹Key Laboratory of Molecule Synthesis and Function Discovery, Fujian Province University, College of Chemistry at Fuzhou University, Fuzhou, Fujian 350108, China.

Accounts of Chemical Research

|April 14, 2021

Summary

This summary is machine-generated.

This study explores novel transformations of organoboron compounds using tetracoordinate boron intermediates to create carbon-boron and carbon-carbon bonds. New methods enable precise bond construction and the development of chiral catalysts for asymmetric synthesis.

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Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides

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Published on: May 26, 2019

Area of Science:

Organic Chemistry
Synthetic Chemistry
Organoboron Chemistry

Background:

Organoboron compounds are versatile reagents for forming carbon-carbon and carbon-heteroatom bonds.
Transformations typically involve tetracoordinate boron intermediates, but current methods face limitations in activation modes, reaction strategies, and stereoselective control.

Purpose of the Study:

To present recent advances in unconventional transformations of organoboron compounds.
To highlight the design of novel tetracoordinate boron intermediates for synthetic applications.
To focus on the construction of C-B bonds, C-C bonds, and the development of chiral tetracoordinate boron species.

Main Methods:

Development of tandem reactions for selective borylation of alkynes and synthesis of stable tetracoordinate boron.
Utilizing domino-borylation-protodeboronation (DBP) strategy and copper-catalyzed diborylation of β-CF3-1,3-enynes.
Employing cascade cross-metathesis and C-H bond borylation, alongside novel coupling partners and chiral Brønsted acid catalysis.

Main Results:

Successful construction of diverse C-B bonds via selective borylation strategies.
Efficient formation of C-C bonds through novel migration reactions and cross-coupling methods, including atroposelective transformations.
Design and application of a chiral tetracoordinate boron complex as a Brønsted acid for highly enantioselective asymmetric catalytic reduction of indoles.

Conclusions:

Unconventional transformations of organoboron compounds, based on designed tetracoordinate boron intermediates, enable precise C-B and C-C bond construction.
A novel chiral Brønsted acid catalyst has been developed for challenging asymmetric catalytic reductions.
These advancements expand the synthetic utility of organoboron compounds and stereoselective synthesis.