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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.

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.

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...

Nomenclature of Aryl and Heterocyclic Amines

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The simplest aromatic amine is phenylamine, which contains an –NH2 functionality directly attached to an aromatic ring. The name aniline is designated for this skeleton. As shown in Figure 1, the common names of the functionalized anilines involve prefixes ortho-, meta-, and para- to indicate the substitution position. Different functionalized aniline derivatives also have notable trivial names.

Formation of Complex Ions

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A type of Lewis acid-base chemistry involves the formation of a complex ion (or a coordination complex) comprising a central atom, typically a transition metal cation, surrounded by ions or molecules called ligands. These ligands can be neutral molecules like H2O or NH3, or ions such as CN− or OH−. Often, the ligands act as Lewis bases, donating a pair of electrons to the central atom. These types of Lewis acid-base reactions are examples of a broad subdiscipline called coordination...

Complexation Equilibria: Overview

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Complexation reactions take place when dative or coordinate covalent bonds form between metal ions and ligands. The compounds formed in these reactions are called coordination compounds. The number of bonds formed between the metal ion and the ligands is called its coordination number. Generally, most metal ions in an aqueous solution are solvated by water molecules and thus exist as aqua complexes.
The equilibrium constant of the complexation reaction is represented as the formation constant...

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AuB₈^-: an Au-borozene complex.

Wei-Jia Chen¹, Yang-Yang Zhang², Wan-Lu Li²

¹Department of Chemistry, Brown University, Providence, RI 02912, USA. lai-sheng_wang@brown.edu.

Chemical Communications (Cambridge, England)

|February 16, 2022

Summary

This summary is machine-generated.

This study reveals the unique chair-like structure of the gold-boron cluster AuB₈^-. Researchers found it features a gold cation bonded to a doubly aromatic borozene dianion, forming novel gold-borozene interactions.

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Area of Science:

Inorganic chemistry
Computational chemistry
Spectroscopy

Background:

Boron clusters are known for their unique structures and bonding.
Understanding metal-boron interactions is crucial for developing new materials.

Purpose of the Study:

To investigate the structure and bonding of the anionic gold-boron cluster, AuB₈^-.
To characterize the nature of the interaction between gold and the boron framework.

Main Methods:

Photoelectron spectroscopy was employed to probe the electronic properties of AuB₈^-.
Quantum chemistry calculations, including global minimum structure searches, were performed.
Chemical bonding analyses were conducted to understand the electronic interactions.

Main Results:

The global minimum structure search identified a stable chair-like configuration for AuB₈^-.
The structure can be described as a gold(I) cation (Au⁺) interacting with a B₈^2- borozene ring.
The bonding involves the gold cation coordinated to the edge of the aromatic B₈^2- ring (Au⁺[η²-B₈^2-]).

Conclusions:

AuB₈^- represents a novel class of borozene complexes.
The study highlights unique gold-borozene bonding characteristics.
This work expands the understanding of metal-boron cluster chemistry.