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Introduction
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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions
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HOTf-Catalyzed Alkyl-Heck-type Reaction.

Huan Zhou1, Liang Ge1, Jinshuai Song2

  • 1State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, 155 Yangqiao Road West, Fuzhou, Fujian 350002, People's Republic of China; University of Chinese Academy of Sciences, Beijing 100049, People's Republic of China.

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|November 15, 2018
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Summary

Researchers developed a novel Brønsted acid-catalyzed Heck-type reaction using carboxylic acids and alkyl peroxides. This efficient method exclusively yields E-alkenes and can be applied to complex natural products.

Keywords:
Natural Product SynthesisOrganic Chemistry MethodsOrganic Synthesis

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • The Heck reaction and its variants have significantly advanced organic synthesis over the past 50 years.
  • Existing Heck-type reactions primarily involve metal catalysis, photo-induction, or base mediation.
  • Brønsted acid-catalyzed Heck-type reactions remain an underexplored area in synthetic chemistry.

Purpose of the Study:

  • To develop a novel one-pot Brønsted acid-catalyzed Heck-type reaction.
  • To utilize readily available aliphatic carboxylic acids as starting materials.
  • To achieve exclusive formation of E-alkenes via a new catalytic pathway.

Main Methods:

  • Employing alkyl peroxides as key intermediates in the reaction.
  • Utilizing triflic acid (HOTf) as a crucial Brønsted acid catalyst.
  • Conducting mechanistic studies using both experimental and computational approaches.

Main Results:

  • Successful application of primary, secondary, and tertiary aliphatic carboxylic acids.
  • Exclusive or highly selective formation of E-alkenes in most cases.
  • Demonstration of the reaction's utility in the direct alkylation of complex natural products.

Conclusions:

  • A new, efficient Brønsted acid-catalyzed Heck-type reaction has been established.
  • The reaction proceeds via a mechanism supported by experimental and computational evidence.
  • This methodology offers a versatile tool for alkene synthesis and functionalization, with potential applications in natural product synthesis.