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Updated: May 16, 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

アミン媒介の電離性アレンボリレーションのメカニズム研究と,MIDAボロナート合成におけるその応用

Viktor Bagutski1, Alessandro Del Grosso, Josue Ayuso Carrillo

  • 1Department of Chemistry, University of Manchester, Manchester, M13 9PL, United Kingdom.

Journal of the American Chemical Society
|December 5, 2012
PubMed
まとめ

アレンとヘテロアレンの直接の電離性ボリレーションは,Y(2) BClとAlCl(3) をアミンで使って達成される. この方法は,安定したMIDA-ボロナートを生成し,活性化基質のためのボレニウムカチオンを持つS(E) Arメカニズムを経由して進行します.

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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.
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Preparation of Amines: Reductive Amination of Aldehydes and Ketones

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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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