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Related Concept Videos

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

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.
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.
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
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.
Preparation of Alcohols via Addition Reactions02:15

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...
Heterogeneous Catalysis01:22

Heterogeneous Catalysis

Heterogeneous catalysis involves a catalyst in a different phase from the reactants. It is a process where the catalyst and the reactants are in distinct phases, typically solid and gas or liquid.Most heterogeneous catalysts are metals, metal oxides, or acids. The list includes transition metals like iron (Fe), cobalt (Co), nickel (Ni), palladium (Pd), platinum (Pt), chromium (Cr), manganese (Mn), tungsten (W), silver (Ag), and copper (Cu). These metals possess partially vacant d orbitals that...

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High-throughput optimization of Ir-catalyzed C-H borylation: a tutorial for practical applications.

Sean M Preshlock1, Behnaz Ghaffari, Peter E Maligres

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

Journal of the American Chemical Society
|March 29, 2013
PubMed
Summary

High-throughput screening optimized iridium-catalyzed C-H borylations by testing various conditions. This research identified key factors for challenging substrates, improving catalytic efficiency.

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Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Synthetic Organic Chemistry

Background:

  • Iridium-catalyzed C-H borylation is a crucial transformation in organic synthesis.
  • Optimizing reaction conditions is essential for efficient and selective borylation.
  • Standard catalytic conditions often face limitations with certain substrates.

Purpose of the Study:

  • To systematically assess the efficiency of iridium-catalyzed C-H borylations.
  • To identify optimal reaction parameters including precatalyst, boron reagent, ligand, and solvent.
  • To uncover novel conditions for challenging substrates.

Main Methods:

  • Utilized high-throughput screening (HTS) to evaluate multiple reaction variables concurrently.
  • Investigated the impact of precatalyst, boron reagent, ligand, order of addition, temperature, solvent, and substrate.
  • Performed systematic variation of reaction components and conditions.

Main Results:

  • Validated established practices in iridium-catalyzed C-H borylation.
  • Discovered unconventional reaction conditions that significantly improved substrate performance.
  • Identified specific parameters critical for borylation efficiency across diverse substrates.

Conclusions:

  • The study provides valuable insights into optimizing iridium-catalyzed C-H borylations.
  • Findings will guide the development of new catalytic systems for difficult substrates.
  • This work advances the scope and applicability of C-H borylation chemistry.