Synthesis
DOI: 10.1055/a-1679-8205
review

Triflic Anhydride (Tf2O)-Activated Transformations of Amides, Sulfoxides and Phosphorus Oxides via Nucleophilic Trapping

Hai Huang
a  Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, School of Petrochemical Engineering, Changzhou University, Changzhou 213164, P. R. of China
,
Jun Yong Kang
b  Department of Chemistry and Biochemistry, University of Nevada Las Vegas, 4505 South Maryland Parkway, Las Vegas, NV 89154-4003, USA
› Author Affiliations
This work was supported by the University of Nevada Las Vegas.


Abstract

Trifluoromethanesulfonic anhydride (Tf2O) is utilized as a strong electrophilic activator in a wide range of applications in synthetic organic chemistry, leading to the transient generation of a triflate intermediate. This versatile triflate intermediate undergoes nucleophilic trapping with diverse nucleophiles to yield novel compounds. In this review, we describe the features and applications of triflic anhydride in organic synthesis reported in the past decade, especially in amide, sulfoxide, and phosphorus oxide chemistry through electrophilic activation. A plausible mechanistic pathway for each important reaction is also discussed.

1 Introduction

2 Amide Chemistry

2.1 Carbon Nucleophiles

2.2 Hydrogen Nucleophiles

2.3 Nitrogen Nucleophiles

2.4 Oxygen and Sulfur Nucleophiles

2.5 hosphorus Nucleophiles

2.6 A Vilsmeier-Type Reagent

2.7 Umpolung Reactivity in Amides

3 Sulfoxide Chemistry

3.1 Oxygen Nucleophiles

3.2 Carbon Nucleophiles

3.3 Nitrogen Nucleophiles

3.4 Thionium Reagents

4 Phosphorus Chemistry

4.1 Hendrickson’s Reagent

4.2 Diaryl Phosphine Oxides

4.3 Phosphonates, Phosphates and Phosphinates

5 Conclusion and Outlook



Publication History

Received: 08 September 2021

Accepted after revision: 27 October 2021

Publication Date:
27 October 2021 (online)

© 2021. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 
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