Synlett 2018; 29(18): 2337-2341
DOI: 10.1055/s-0037-1610550
synpacts
© Georg Thieme Verlag Stuttgart · New York

Uncovering Multifaceted Iodonium Ylides: Versatile Reactivity Enables Cyclization of Simple Arylamines

Liang Zhang
School of Chemistry and Chemical Engineering & Key Laboratory of the Colloid and Interface Chemistry, Shandong University, 27 Shanda Nanlu, Jinan 250100, Shandong, P. R. of China   Email: yaowang@sdu.edu.cn
,
Yao Wang  *
School of Chemistry and Chemical Engineering & Key Laboratory of the Colloid and Interface Chemistry, Shandong University, 27 Shanda Nanlu, Jinan 250100, Shandong, P. R. of China   Email: yaowang@sdu.edu.cn
› Author Affiliations
We gratefully acknowledge the National Natural Science Foundation of China (21772113, 21302075, 11501454), The Key Research and ­Development Plan of Shandong Province (2017GGX70109), The ­Fundamental Research Fund of Shandong University (2017JC004).
Further Information

Publication History

Received: 14 June 2018

Accepted after revision: 07 July 2018

Publication Date:
02 August 2018 (online)


Abstract

Iodonium ylides can undergo cyclization with a simple tertiary arylamine to afford N-heterocyclic products in a transition-metal-free approach in the absence of an additional initiator/oxidant. The ­inherent reactivity uncovered in this transformation is fundamentally different from known chemical properties of iodonium ylide compounds, thus providing a new opportunity for the further exploration of iodonium ylide-based chemical transformations. This Synpacts article describes the historical background of iodonium ylide chemistry and highlights recent progress disclosed by our work.

1 Introduction

2 The Strategy for New Reaction Discovery

3 Application to Cyclization of Tertiary Arylamines

4 Conclusion and Perspectives

 
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