Journal
SYNTHESIS-STUTTGART
Volume 51, Issue 5, Pages 985-1005Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0037-1611659
Keywords
Heck reaction; cross-coupling; alkyl halides; alkenes; transition-metal catalysis
Categories
Funding
- National Institutes of Health [GM120281]
- National Science Foundation [CHE-1663779]
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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 alpha-Carbonyl Alkyl Halides 2.3 Fluoroalkyl Halides 2.4 alpha-Functionalized Alkyl Halides 2.5 Unactivated Alkyl Electrophiles 3 Ni-Catalyzed Heck-Type Reactions 3.1 Benzylic Electrophiles 3.2 alpha-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
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