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相关概念视频

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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Updated: Jul 4, 2026

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

Published on: November 30, 2022

胺基导向化:范围和局限性

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
概括
此摘要是机器生成的。

激活使氨基酸中的分子内酸化成为可能,从而提供区域化学控制. 这种方法避免了反复化,并且根据碳链长度显示出不同的选择性.

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科学领域:

  • 有机化学 有机化学
  • 有机金属化学 有机金属化学

背景情况:

  • 化是一种关键的有机转化.
  • 控制不和氨基酸在化过程中的区域选择性是具有挑战性的.
  • 现有的方法往往缺乏精确的控制或涉及恶劣的条件.

研究的目的:

  • 为了研究同样性和双同样性氨基的诱导的分子内化.
  • 为了将激活反应的区域选择性与使用四基 (THF·BH3) 的对照实验进行比较.
  • 阐明反应机制和长度对选择性的影响.

主要方法:

  • 使用激活氨基玻兰的激活.
  • 乳标记研究探测反应途径.
  • 在不同的激活条件和基质结构下对区域选择性的比较分析.

主要成果:

  • 激活促进同样性和双同样性氨基的分子内化,具有良好的至优良的区域化学控制.
  • 反应通过一种内部分子机制进行,类似于经典的4中心过程,并且不可逆转.
  • 区域选择性受碳链长度的影响,较短的带有利于分子间反应,较长的带显示选择性下降.

结论:

  • 以为媒介的化提供了一种可控的方法来功能化氨基.
  • 反应机制与经典的化不同,对基质结构敏感.
  • 这种方法为合成特定的有机化合物提供了有价值的替代方案.