Transition-Metal-Catalyzed Alkyl Heck-Type Reactions

Published as part of the 50 Years SYNTHESIS – Golden Anniversary Issue

‡ These authors contributed equally.

Abstract

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

Key words

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

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