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

Liang Zhang; Yao Wang

doi:10.1055/s-0037-1610550

Synlett, Table of Contents

Synlett 2018; 29(18): 2337-2341
DOI: 10.1055/s-0037-1610550

synpacts

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

Abstract

All articles of this category

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

Key words

iodonium ylide - tertiary arylamine - cyclization - N-heterocycle - electron transfer

Full Text

References

References

1a Stang PJ. Zhdankin VV. Chem. Rev. 1996; 96: 1123
1b Zhdankin VV. Stang PJ. Chem. Rev. 2002; 102: 2523
1c Zhdankin VV. Hypervalent Iodine Chemistry: Preparation, Structure and Synthetic Applications of Polyvalent Iodine Compounds. Wiley; New York: 2013
1d Yoshimura A. Zhdankin VV. Chem. Rev. 2016; 116: 3328

2 Muller P. Acc. Chem. Res. 2004; 37: 243

3a Ochiai M. Kitagawa Y. Yamamoto S. J. Am. Chem. Soc. 1997; 119: 11598
3b Huang X.-C. Liu Y.-L. Liang Y. Pi S.-F. Wang F. Li J.-H. Org. Lett. 2008; 10: 1525
3c Antos A. Elemes Y. Michaelides A. Nyxas JA. Skoulika S. Hadjiarapoglou LP. J. Org. Chem. 2012; 77: 10949
3d Huang H. Yang Y. Zhang X. Zeng W. Liang Y. Tetrahedron Lett. 2013; 54: 6049

4 Chelli S. Troshin K. Mayer P. Lakhdar S. Ofial AR. Mayr H. J. Am. Chem. Soc. 2016; 138: 10304

5a Zhdankin VV. Stang PJ. Chem. Rev. 2008; 108: 5299
5b Malamidou-Xenikaki E. Spyroudis S. Synlett 2008; 2725

6 Saito M. Kobayashi Y. Tsuzuki S. Takemoto Y. Angew. Chem. Int. Ed. 2017; 56: 7653

For an early report on the rearrangement reaction of halonium ylides, see:

7a Kirmse W. Kapps M. Hager RB. Chem. Ber. 1966; 99: 2855
7b For an early report on the rearrangement reaction of iodonium ylides, see: Doyle MP. Tamblyn WH. Bagheri V. J. Org. Chem. 1981; 46: 5094

8a Xu B. Tambar UK. J. Am. Chem. Soc. 2016; 138: 12073
8b Xu B. Tambar UK. Angew. Chem. Int. Ed. 2017; 56: 9868

9 Wang X. Studer A. Acc. Chem. Res. 2017; 50: 1712

10a Hartmann M. Li Y. Mick-Lichtenfeld C. Studer A. Chem. Eur. J. 2016; 22: 3485
10b Telu S. Durmus S. Koser GF. Tetrahedron Lett. 2007; 48: 1863

11 Heinen F. Engelage E. Dreger A. Weiss R. Huber SM. Angew. Chem. Int. Ed. 2018; 57: 3830
12 Zhao Z. Luo Y. Liu S. Zhang L. Feng L. Wang Y. Angew. Chem. Int. Ed. 2018; 57: 3792

13a Wu Y.-J. Heterocyclic Scaffolds II: Topics in Heterocyclic Chemistry, Vol. 26 . Gribble GW. Springer; Heidelberg: 2010
13b Pan SC. Beilstein J. Org. Chem. 2012; 8: 1374
13c Peng B. Maulide N. Chem. Eur. J. 2013; 19: 13274
13d Haibach MC. Seidel D. Angew. Chem. Int. Ed. 2014; 53: 5010
13e Yi H. Zhang G. Wang H. Huang Z. Wang J. Singh AK. Lei A. Chem. Rev. 2017; 117: 9016

14 Zhou B. Chen Z. Yang Y. Ai W. Tang H. Wu Y. Zhu W. Li Y. Angew. Chem. Int. Ed. 2015; 54: 12121