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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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Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

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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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Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

9.4K
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.
9.4K
Anionic Chain-Growth Polymerization: Overview01:20

Anionic Chain-Growth Polymerization: Overview

2.6K
The polymerization process that involves carbanion as an intermediate is called anionic polymerization. It is also a type of addition or chain-growth polymerization. Anionic polymerization gets initiated by a strong nucleophile such as an organolithium or a Grignard reagent. The most commonly used initiator for anionic polymerization is butyl lithium. Monomers involved in anionic polymerization must possess a vinyl group bonded to one or two electron-withdrawing groups. For instance,...
2.6K
Preparation of Amines: Reductive Amination of Aldehydes and Ketones01:38

Preparation of Amines: Reductive Amination of Aldehydes and Ketones

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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.
3.7K
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

7.3K
All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
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Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
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Anionic Iminoborane as Boryl Anion Synthon.

Yuyang Dai1, Ping Cui1, Chen-Ho Tung1

  • 1School of Chemistry and Chemical Engineering, Shandong University, Jinan, 250100, China.

Angewandte Chemie (International Ed. in English)
|September 17, 2025
PubMed
Summary
This summary is machine-generated.

Researchers developed a novel anionic iminoborane with unique reactivity. This versatile compound acts as both a nucleophilic boryl anion synthon and a BNC-1,3-dipole for diverse organoboron synthesis.

Keywords:
BNC‐1,3‐dipoleBoron functionalizationBoryl anion synthonCooperative reactivityIminoborane

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Area of Science:

  • Organoboron Chemistry
  • Synthetic Chemistry

Background:

  • Classical iminoboranes exhibit 1,2-dipolar reactivity with an electrophilic boron center.
  • Research on iminoboranes has been ongoing since the 1980s.

Purpose of the Study:

  • To report a novel anionic iminoborane with cooperative reactivity.
  • To explore its potential as a nucleophilic boryl anion synthon and a BNC-1,3-dipole.

Main Methods:

  • Synthesis of an anionic iminoborane, [Ar─B≡N─Flu]-, featuring a fluorenyl anion substitution at nitrogen.
  • Investigating its reactivity with N-, P-, Se-, and Au-based electrophiles.
  • Examining its participation in [3 + n] cycloadditions.

Main Results:

  • The anionic iminoborane displays cooperative reactivity due to a conjugative B≡N─C: unit.
  • It functions as a nucleophilic boryl anion synthon, reacting via carbanion attack and 1,3-migration.
  • It also acts as a BNC-1,3-dipole, participating in cycloaddition reactions.

Conclusions:

  • A rationally designed anionic iminoborane offers versatile reactivity beyond classical iminoboranes.
  • This compound serves as a platform for constructing diverse organoboron architectures.
  • The study expands the scope of iminoborane chemistry.