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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.
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

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Introduction
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Fabricating Superhydrophobic Polymeric Materials for Biomedical Applications
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Published on: August 28, 2015

Macrolactonization via hydrocarbon oxidation.

Kenneth J Fraunhoffer1, Prabagaran Narayanasamy, Lauren E Sirois

  • 1Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, Illinois 61801, USA.

Journal of the American Chemical Society
|July 13, 2006
PubMed
Summary

A new palladium-catalyzed reaction enables macrolactonization of omega-alkenoic acids. This efficient method demonstrates broad substrate scope and high functional group tolerance, useful for complex molecule synthesis.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Macrolactonization is a crucial transformation in synthesizing complex natural products and pharmaceuticals.
  • Existing methods often require harsh conditions or lack broad functional group compatibility.

Purpose of the Study:

  • To develop a novel, efficient, and broadly applicable palladium-catalyzed macrolactonization reaction.
  • To investigate the reaction mechanism and scope for synthesizing diverse lactones.

Main Methods:

  • Utilized a novel Pd/sulfoxide catalytic system for macrolactonization of linear omega-alkenoic acids.
  • Employed serial ligand-catalyzed allylic C-H oxidation pathway.
  • Investigated reaction scope with various aryl, alkyl, and unsaturated acids, and assessed functional group compatibility.

Main Results:

  • Achieved efficient macrolactonization of omega-alkenoic acids via a novel Pd/sulfoxide catalytic system.
  • Demonstrated broad substrate scope, including (Z)-alpha,beta-unsaturated acids without isomerization.
  • Showcased high functional group compatibility with biologically relevant moieties like peptides and esters.

Conclusions:

  • The reported Pd/sulfoxide-catalyzed reaction provides a powerful new tool for macrolactone synthesis.
  • The reaction proceeds via inner-sphere functionalization from a templated pi-allylPd carboxylate intermediate.
  • This methodology offers significant advantages in terms of efficiency, scope, and functional group tolerance for complex molecule synthesis.