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関連する概念動画

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.
Electrophilic 1,2- and 1,4-Addition of HX to 1,3-Butadiene01:17

Electrophilic 1,2- and 1,4-Addition of HX to 1,3-Butadiene

The electrophilic addition of hydrogen halides such as HBr to alkenes and nonconjugated dienes gives a single product as per Markovnikov’s rule.
Halogenation of Alkenes02:46

Halogenation of Alkenes

Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene01:14

Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene

Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.
Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

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,...

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関連する実験動画

Updated: May 21, 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

イリジウムC-Hボリレーションにおける外球方向.

Philipp C Roosen1, Venkata A Kallepalli, Buddhadeb Chattopadhyay

  • 1Department of Chemistry, Michigan State University, East Lansing, Michigan 48824-1322, USA.

Journal of the American Chemical Society
|June 19, 2012
PubMed
まとめ
この要約は機械生成です。

NHBocグループは,アレンとアルケンの選択的C-Hボリレーションを可能にします. この外球メカニズムは水素結合を含み,指向性オーソメタレーションを補完するユニークな地域選択性を提供します.

さらに関連する動画

Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene
09:45

Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene

Published on: March 20, 2017

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
04:38

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions

Published on: July 28, 2022

関連する実験動画

Last Updated: May 21, 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

Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene
09:45

Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene

Published on: March 20, 2017

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
04:38

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions

Published on: July 28, 2022

科学分野:

  • 有機化学 オーガニック・ケミストリー
  • カタリシス カタリシス カタリシス

背景:

  • 誘導性オーソメタレーションは,アロマティックリングの機能化のために一般的です.
  • C-Hボリレーションは,ボロンの機能群を導入するための強力なツールです.
  • 地域選択的なC-H機能化のための新しい方法の開発は極めて重要です.

研究 の 目的:

  • オーソセレクティブC-HボリレーションのNHBoc群を導入する.
  • この新しいボリレーション反応のメカニズムを解明するために.
  • 地域選択性を,指向性オーソメタレーションなどの既存の方法と比較する.

主な方法:

  • アレンとアルケンの実験研究.
  • 反応メカニズムを理解するための計算による調査.
  • C-Hボリレーション反応における地域選択性の分析.

主要な成果:

  • NHBocグループは,オーソセレクティブC-Hボリレーションを成功裏に導いた.
  • 外界球のメカニズムが提案され,データで裏付けられました.
  • ボリルリガンドの酸素にN-H陽子の水素結合が鍵であると特定されました.
  • ダイレクトされたオーソメタレーションとは異なるユニークな地域選択性が観察されました.

結論:

  • NHBocグループは,地域選択的C-Hボリレーションのための効果的な指導グループです.
  • 外界球のメカニズムは,C-H機能化に関する新しいメカニズム的洞察を提供します.
  • この方法は,確立されたオルト機能化の技術に補完的な地域選択性を提供します.