Transition-Metal-Catalyzed Alkyl Heck-Type Reactions

Daria Kurandina, Padon Chuentragool, Vladimir Gevorgyan

Research output: Contribution to journalReview articlepeer-review

70 Scopus citations


The Heck reaction is one of the most reliable and useful strategies for the construction of C-C bonds in organic synthesis. However, in contrast to the well-established aryl Heck reaction, the analogous reaction employing alkyl electrophiles is much less developed. Significant progress in this area was recently achieved by merging radical-mediated and transition-metal-catalyzed approaches. This review summarizes the advances in alkyl Heck-type reactions from its discovery early in the 1970s up until the end of 2018. 1 Introduction 2 Pd-Catalyzed Heck-Type Reactions 2.1 Benzylic Electrophiles 2.2 α-Carbonyl Alkyl Halides 2.3 Fluoroalkyl Halides 2.4 α-Functionalized Alkyl Halides 2.5 Unactivated Alkyl Electrophiles 3 Ni-Catalyzed Heck-Type Reactions 3.1 Benzylic Electrophiles 3.2 α-Carbonyl Alkyl Halides 3.3 Unactivated Alkyl Halides 4 Co-Catalyzed Heck-Type Reactions 5 Cu-Catalyzed Heck-Type Reactions 6 Other Metals in Heck-Type Reactions 7 Conclusion.

Original languageEnglish (US)
Pages (from-to)985-1005
Number of pages21
JournalSynthesis (Germany)
Issue number5
StatePublished - 2019
Externally publishedYes


  • Heck reaction
  • alkenes
  • alkyl halides
  • cross-coupling
  • transition-metal catalysis

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry


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