Synthesis 2017; 49(15): 3183-3214
DOI: 10.1055/s-0036-1588452
review
© Georg Thieme Verlag Stuttgart · New York

Keteniminium Ions: Unique and Versatile Reactive Intermediates for Chemical Synthesis

Gwilherm Evano*, Morgan Lecomte, Pierre Thilmany, Cédric Theunissen
  • Laboratoire de Chimie Organique, Service de Chimie et PhysicoChimie Organiques, Université libre de Bruxelles (ULB), Avenue F. D. Roosevelt 50, CP160/06, 1050 Brussels, Belgium   Email: gevano@ulb.ac.be
Our work was supported by the Université libre de Bruxelles (ULB) and the FNRS (CDR J.0058.17 Keteniminium). M.L. and C.T. acknowledge the Fonds pour la formation à la Recherche dans l’Industrie et dans l’Agriculture (F.R.I.A.) for graduate fellowships
Further Information

Publication History

Received: 15 May 2017

Accepted after revision: 16 May 2017

Publication Date:
17 July 2017 (eFirst)

Dedicated to Prof. Herbert Mayr, a truly inspiring chemist, on the occasion of his 70th birthday

Abstract

Keteniminium ions have been demonstrated to be remarkably useful and versatile reactive intermediates in chemical synthesis. These unique heterocumulenes are pivotal electrophilic species involved in a number of efficient and selective transformations. More recently, even more reactive ‘activated’ keteniminium ions bearing an additional electron-withdrawing group on the nitrogen atom have been extensively investigated. The chemistry of these unique reactive intermediates, including representative methods for their in situ generation, will be overviewed in this review article.

1 Introduction

2 The Chemistry of Keteniminium Ions

3 The Chemistry of Activated Keteniminium Ions

4 Keteniminium Ions: Pivotal Intermediates for the Synthesis of Natural and/or Biologically Relevant Molecules

5 Conclusions and Perspectives