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Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

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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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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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Alcohols from Carbonyl Compounds: Reduction02:23

Alcohols from Carbonyl Compounds: Reduction

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Reduction is a simple strategy to convert a carbonyl group to a hydroxyl group. The three major pathways to reduce carbonyls to alcohols are catalytic hydrogenation, hydride reduction, and borane reduction.
Catalytic hydrogenation is similar to the reduction of an alkene or alkyne by adding H2 across the pi bond in the presence of transition metal catalysts like Raney Ni, Pd–C, Pt, or Ru. Aldehydes and ketones can be reduced by this method, often under mild to moderate heat (25–100°C) and...
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Regioselectivity and Stereochemistry of Hydroboration02:36

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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.
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Preparation of Alcohols via Addition Reactions02:15

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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...
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Preparation of Amines: Reductive Amination of Aldehydes and Ketones01:38

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Carbonyl compounds and primary amines undergo reductive amination first to produce imines, followed by secondary amines in the same reaction mixture, using selective reducing agents like sodium cyanoborohydride or sodium triacetoxyborohydride. Reductive amination produces different degrees of substitution of amines depending on the starting amine substrate.
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Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
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A Mild Method for Making MIDA Boronates.

Aidan M Kelly1, Peng-Jui Chen1, Jenna Klubnick1

  • 1Roger Adams Laboratory, School of Chemical Sciences, University of Illinois at Urbana-Champaign, 600 S, Mathews Avenue, Urbana, Illinois 61801, United States.

Organic Letters
|August 26, 2020
PubMed
Summary
This summary is machine-generated.

A new MIDA anhydride method simplifies MIDA boronate synthesis. This approach enables the preparation of sensitive boronates using readily available lab equipment, making MIDA boronate synthesis more accessible.

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Area of Science:

  • Organic Synthesis
  • Boronate Chemistry

Background:

  • Methyliminodiacetic acid (MIDA) boronates are valuable synthetic intermediates.
  • Existing methods for MIDA boronate synthesis can be complex and require specialized reagents or conditions.

Purpose of the Study:

  • To develop a mild, simple, and broadly applicable method for MIDA boronate synthesis.
  • To expand the range of sensitive boronic acids that can be converted into MIDA boronates.
  • To create a user-friendly kit for MIDA boronate preparation.

Main Methods:

  • Utilized a predried form of methyliminodiacetic acid (MIDA), MIDA anhydride, as both a MIDA ligand source and an in situ desiccant.
  • Developed a MIDA Boronate Maker Kit for direct preparation and purification of MIDA boronates from boronic acids.
  • Employed simple heating and centrifugation for MIDA boronate synthesis.

Main Results:

  • Established a mild and straightforward MIDA boronate synthesis procedure.
  • Successfully converted a wider range of sensitive boronic acids into their MIDA boronate derivatives.
  • Demonstrated the efficacy of the MIDA Boronate Maker Kit for accessible MIDA boronate preparation.

Conclusions:

  • MIDA anhydride offers a convenient and effective reagent for MIDA boronate synthesis.
  • The MIDA Boronate Maker Kit democratizes MIDA boronate preparation for laboratories lacking specialized organic synthesis equipment.