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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.
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.
Radical Anti-Markovnikov Addition to Alkenes: Overview01:25

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.
Preparation of Alcohols via Addition Reactions02:15

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 and Stereochemistry of Acid-Catalyzed Hydration02:34

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.

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Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
08:56

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

Published on: November 30, 2022

アミンの誘導による水酸化:範囲と限界

Matthew Scheideman1, Guoqiang Wang, Edwin Vedejs

  • 1Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, USA.

Journal of the American Chemical Society
|June 14, 2008
PubMed
まとめ
この要約は機械生成です。

ヨウ素の活性化により,アミンボランの分子内水酸化が可能になり,地域化学的制御が可能になります. この方法は,逆水酸化を回避し,炭素鎖の長さに基づいて選択性が異なる.

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A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
07:06

A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis

Published on: February 16, 2020

Achieving Moderate Pressures in Sealed Vessels Using Dry Ice As a Solid CO2 Source
06:26

Achieving Moderate Pressures in Sealed Vessels Using Dry Ice As a Solid CO2 Source

Published on: August 17, 2018

関連する実験動画

Last Updated: Jul 4, 2026

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
08:56

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

Published on: November 30, 2022

A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
07:06

A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis

Published on: February 16, 2020

Achieving Moderate Pressures in Sealed Vessels Using Dry Ice As a Solid CO2 Source
06:26

Achieving Moderate Pressures in Sealed Vessels Using Dry Ice As a Solid CO2 Source

Published on: August 17, 2018

科学分野:

  • 有機化学 オーガニック・ケミストリー
  • 有機金属化学 有機金属化学

背景:

  • ハイドロボレーションは重要な有機変換である.
  • 不飽和アミンボランの水酸化における地域選択性の制御は難しい.
  • 既存の方法は,しばしば正確な制御がないか,厳しい条件を伴う.

研究 の 目的:

  • ホモアリル系およびバイスホモアリル系アミンボランのヨウ素誘発の分子内水酸化を調査する.
  • テトラヒドロフランボラン (THF·BH3) を使用したコントロール実験とヨウ素活性化反応の地域選択性を比較する.
  • 反応機構の解明とセレクティブ性に対するテザー長さの影響.

主な方法:

  • ヨウ素を用いたアミンボランの活性化.
  • 反応経路を調査するデウテリウムラベリングの研究.
  • 異なる活性化条件と基板構造の下での地域選択性の比較分析.

主要な成果:

  • ヨウ素の活性化により,ホモアリルおよびバイスホモアリルアミンボランの分子内水酸化が促進され,良好から優れた地域化学的制御が得られます.
  • この反応は,古典的な4中心のプロセスに類似した分子内メカニズムを経由して進行し,逆戻りはできません.
  • 地域選択性は,炭素鎖の長さに影響され,より短い鎖は分子間反応を好み,より長い鎖は選択性の低下を示します.

結論:

  • ヨウ素媒介による水酸化は,アミンボランを機能化する制御された方法を提供します.
  • 反応メカニズムは,古典的な水浸しから異なり,基板構造に敏感です.
  • このアプローチは,特定のオルガノボロン化合物を合成するための貴重な代替手段を提供します.