Acidic Hydrogen-Tethered Electron-Deficient Acceptors for Phosphine-Catalyzed Annulations

Abstract

Nucleophilic phosphine-catalyzed annulations are recognized as practical and powerful tools for synthesizing various cyclic compounds. Phosphine acceptors play a key role in nucleophilic phosphine catalysis. The design and synthesis of new phosphine acceptors that are able to introduce new zwitterionic intermediates with new reactivities into phosphine-catalyzed annulations is highly desirable. We recently applied proton-shift principles in the design of new phosphine acceptors, and we synthesized several new acceptors. With the use of these acceptors, we have developed several novel phosphine-catalyzed annulation reactions. In this account, we present a brief introduction to the design and application of a series of acidic-hydrogen-tethered electron-deficient acceptors for phosphine-catalyzed annulation reactions, categorized according to the type of atom (N–H, O–H, C–H) to which the acidic hydrogen is bound.

1 Introduction

2 Phosphine Acceptors Tethered with an Acidic N–H Group

3 Phosphine Acceptors Tethered with an Acidic O–H Group

4 Phosphine Acceptors Tethered with an Acidic C–H Group

5 Conclusions

Key words

phosphine catalysis - annulation - cyclic compounds - acidic hydrogen - phosphine acceptors

Publication History

Received: 09 December 2023

Accepted after revision: 10 January 2024

Accepted Manuscript online:
10 January 2024

Article published online:
05 February 2024

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