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

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

Content Provider	Scilit
Author	Kang∗, Jun Yong Huang, Hai
Copyright Year	2021
Description	Trifluoromethanesulfonic anhydride $(Tf_{2}$O) 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 Received: 08 September 2021 Accepted after revision: 27 October 2021 Accepted Manuscript online: 27 October 2021 Article published online: 04 January 2022 © 2021. Thieme. All rights reserved Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, Germany
Related Links	http://www.thieme-connect.de/products/ejournals/pdf/10.1055/a-1679-8205.pdf
Ending Page	1202
Page Count	46
Starting Page	1157
ISSN	00397881
e-ISSN	1437210X
DOI	10.1055/a-1679-8205
Journal	Synthesis
Issue Number	05
Volume Number	54
Language	English
Publisher	Georg Thieme Verlag KG
Publisher Date	2021-10-27
Access Restriction	Open
Subject Keyword	Journal: Synthesis Electrophilic Activation Phosphorus Oxides Triflic Anhydride Phosphonium Triflate
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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