関連する実験動画

Updated: Apr 23, 2026

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

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

Published on: November 30, 2022

鉄で触媒化されたC (((sp (((2)) -H結合の機能化は,オルガンボロン化合物と作用する

Rui Shang¹, Laurean Ilies, Sobi Asako

¹Department of Chemistry, School of Science, The University of Tokyo , 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.

Journal of the American Chemical Society

|October 1, 2014

まとめ

この研究では,様々な基板とオルガンボロン化合物を結合するための鉄触媒C-H機能化の方法が紹介されています. 反応は,C-H結合の活性化と効率的な結合に不可欠な有機鉄 (III) の中間体を通して進行します.

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
有機金属化学有機金属化学

背景:

C-H機能化は有機合成の重要な戦略である.
C-H活性化のための効率的な触媒システムの開発は,依然として大きな課題です.
オーガノボロン化合物は,多用途の結合パートナーである.

研究の目的:

新しい鉄触媒C-H機能化反応を開発する.
様々なアロマティック,ヘテロアロマティック,オレフィン基板の結合を可能にする.
軽度な条件下でオーガノボロン化合物を結合パートナーとして利用する.

主な方法:

鉄で触媒化されたC-H機能化.
酸化結合反応の条件.
アロマティック,ヘテロアロマティック,オレフィン基板を使用しています.
アルケニルおよびアリルボロン化合物を使用します.
亜鉛塩のプロモーターの役割を調査する.

主要な成果:

多様な基質とオーガノボロン化合物の成功結合.
軽度の酸化反応条件の実証.
オーガノアイロン (III) 中間物質の識別.
C-H結合活性化メカニズムの解明.
触媒サイクルにおける亜鉛塩の重要な役割の確認.

結論:

開発された鉄触媒反応は,C-H機能化のための新しい経路を提供します.
オーガノアイロン (III) の中間体は,C−H結合活性化プロセスの鍵です.
亜鉛塩は,触媒サイクルにおける有機群の移転を促進するために不可欠である.

さらに関連する動画

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS

Published on: June 20, 2014

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides

Published on: May 26, 2019

関連する概念動画

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.

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...

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.

Properties of Organometallic Compounds

Properties of Organometallic Compounds

Organometallic compounds are compounds that contain a carbon–metal bond. Carbon belongs to an organyl group like alkyl, aryl, allyl, or benzyl groups. The metal can be from Group I or Group II of the periodic table, a transition metal, or a semimetal.

Preparation of Alcohols via Addition Reactions

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...

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...