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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.

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation reactions,...

ortho–para-Directing Activators: –CH3, –OH, –&NoBreak;NH2, –OCH3

ortho–para-Directing Activators: –CH₃, –OH, –⁠NH₂, –OCH₃

All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...

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.

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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

Selenium-Directed ortho-C-H Borylation by Iridium Catalysis.

Jia Tang¹, Thishana Singh², Xingzhen Li¹

¹College of Chemistry and Chemical Engineering, Southwest Petroleum University, Xindu Road 8, Chengdu, Sichuan 610500, China.

The Journal of Organic Chemistry

|August 20, 2020

Summary

Selenium now directs ortho-C-H borylation in a novel iridium-catalyzed reaction. This efficient method synthesizes diverse organoselenium compounds using benzyl selenide derivatives.

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Published on: September 12, 2018

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Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes

Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes

Published on: September 12, 2018

Area of Science:

Organometallic Chemistry
Catalysis
Organic Synthesis

Background:

C-H activation and functionalization are crucial in modern organic synthesis.
Directing group strategies are essential for regioselective C-H functionalization.
Selenium's role as a directing group in C-H borylation remains unexplored.

Purpose of the Study:

To develop a novel iridium-catalyzed ortho-C-H borylation reaction.
To investigate selenium as a directing group for C-H borylation.
To establish an efficient synthetic route for organoselenium compounds.

Main Methods:

Iridium-catalyzed reaction utilizing benzyl selenide derivatives.
Employing tricyclohexylphosphine ligand for enhanced catalytic efficiency.
Systematic variation of substrates to assess reaction scope and limitations.

Main Results:

Successful development of selenium-directed ortho-C-H borylation.
Demonstration of selenium's utility as a directing group in C-H borylation.
Good yields of ortho-monoborylated and diborylated products achieved with various substrates.

Conclusions:

This study presents the first example of selenium-directed C-H borylation.
The developed method offers an efficient pathway for synthesizing diverse organoselenium compounds.
The use of tricyclohexylphosphine ligand improves catalytic performance.