Recent Advances in Transition-Metal-Free (4+3)-Annulations

Heather Lam; Xavier Abel-Snape; Martin F. Köllen; Mark Lautens

doi:10.1055/s-0040-1706023

Synthesis, Table of Contents

Synthesis 2021; 53(22): 4134-4177
DOI: 10.1055/s-0040-1706023

special topic

Special Issue dedicated to Prof. Sarah Reisman, recipient of the 2019 Dr. Margaret Faul Women in Chemistry Award

Recent Advances in Transition-Metal-Free (4+3)-Annulations

Authors

Heather Lam ∗

^aDavenport Research Laboratories, Department of Chemistry, University of Toronto, Toronto, Ontario M5S 3H6, Canada
Xavier Abel-Snape

^aDavenport Research Laboratories, Department of Chemistry, University of Toronto, Toronto, Ontario M5S 3H6, Canada
Martin F. Köllen

^bLudwig-Maximilians-Universität München, Department Chemie und Biochemie, Butenandtstr. 5-13, 81377 München, Germany
Mark Lautens∗

^aDavenport Research Laboratories, Department of Chemistry, University of Toronto, Toronto, Ontario M5S 3H6, Canada

Abstract

All articles of this category

Abstract

(4+3)-Annulations are incredibly versatile reactions which combine a 4-atom synthon and a 3-atom synthon to form both 7-membered carbocycles as well as heterocycles. We have previously reviewed transition-metal-catalyzed (4+3)-annulations. In this review, we will cover examples involving bases, NHCs, phosphines, Lewis and Brønsted acids as well as some rare examples of boronic acid catalysis and photocatalysis. In analogy to our previous review, we exclude annulations involving cyclic dienes like furan, pyrrole, cyclohexadiene or cyclopentadiene, as Chiu, Harmata, Fernándes and others have recently published reviews encompassing such substrates. We will however discuss the recent additions (2010–2020) to the literature on (4+3)-annulations involving other types of 4-atom-synthons.

1 Introduction

2 Bases

3 Annulations Using N-Heterocyclic Carbenes

3.1 N-Heterocyclic Carbenes (NHCs)

3.2 N-Heterocyclic Carbenes and Base Dual-Activation

4 Phosphines

5 Acids

5.1 Lewis Acids

5.2 Brønsted Acids

6 Boronic Acid Catalysis and Photocatalysis

7 Conclusion

Key words

annulation - (4+3)-annulations - organocatalysis - Lewis acids - Brønsted acids - phosphines - N-heterocyclic carbenes

Full Text

References

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