Azidation with Hypervalent Iodine Reagents

Raphaël Simonet-Davin; Jerome Waser

doi:10.1055/a-1966-4974

Synthesis, Table of Contents

Synthesis 2023; 55(11): 1652-1661
DOI: 10.1055/a-1966-4974

short review

Special Issue dedicated to Prof. Cristina Nevado, recipient of the 2021 Dr. Margaret Faul Women in Chemistry Award

Azidation with Hypervalent Iodine Reagents

Raphaël Simonet-Davin

,

Jerome Waser ∗

Abstract

All articles of this category

Dedicated to Prof. Cristina Nevado at the occasion of the awarding of the Dr. Margaret Faul Women in Chemistry Award 2021

Abstract

In this short review, we describe applications of hypervalent iodine reagents for the azidation of organic compounds from seminal publications to the most recent reports. After reviewing selected examples of azidations based on the use of in situ formed unstable non-cyclic reagents, we focus in more detail on stable cyclic hypervalent iodine reagents. Important advances in the azidation of C–H bonds, alkenes, as well as other transformations are described. Rather than being comprehensive, we highlight selected key reports that, in our opinion, especially contributed to the advancement of research in the field.

1 Introduction

2 Non-Cyclic λ³-Iodanes

3 Heterocyclic λ³-Iodanes

3.1 Azidation of Aliphatic C–H Bonds

3.2 Azidation of Alkenes

3.3 Other Azidations

4 Conclusion and Outlook

Key words

azidation - hypervalent iodine reagents - metal catalysis - photocatalysis - nucleoazidation - cyclization

Full Text

References

References
1 Griess PJ. Proc. R. Soc. London 1864; 13: 375

2a For a complete review of azides, see: Bräse S, Gil C, Knepper K, Zimmermann V. Angew. Chem. Int. Ed. 2005; 44: 5188
2b For a review on azide modification, see: Huang D, Yan G. Adv. Synth. Catal. 2017; 359: 1600

3 Lao Z, Toy PH. Beilstein J. Org. Chem. 2016; 12: 2577
4 Nyfeler E, Renaud P. Chimia 2006; 60: 276
5 Kolb HC, Finn MG, Sharpless KB. Angew. Chem. Int. Ed. 2001; 40: 2004
6 Staudinger H, Meyer J. Helv. Chim. Acta 1919; 2: 635

7a Saxon E, Bertozzi CR. Science 2000; 287: 2007
7b Saxon E, Armstrong JI, Bertozzi CR. Org. Lett. 2000; 2: 2141

8 Zhang X, Ji A, Wang Z, Lou H, Li J, Zheng L, Zhou Y, Qu C, Liu X, Chen H, Cheng Z. J. Med. Chem. 2021; 64: 11543

9a For a review on the synthesis of aliphatic azides, see: Sivaguru P, Ning Y, Bi X. Chem. Rev. 2021; 121: 4253
9b For a review on Csp³–H radical azidation, see: Ge L, Chiou M.-F, Li Y, Bao H. Green Synth. Catal. 2020; 1: 86

10a For generals reviews on hypervalent iodine, see: Stang PJ, Zhdankin VV. Chem. Rev. 1996; 96: 1123
10b Zhdankin VV, Stang PJ. Chem. Rev. 2008; 108: 5299
10c Yoshimura A, Zhdankin VV. Chem. Rev. 2016; 116: 3328
10d For reviews on original applications in organic synthesis, see: Wirth T. Angew. Chem. Int. Ed. 2005; 44: 3656
10e Ladziata U, Zhdankin VV. ARKIVOC 2006; (ix): 26
10f For a book, see: Zhdankin VV. Hypervalent Iodine Chemistry: Preparation, Structure, and Synthetic Applications of Polyvalent Iodine Compounds. Wiley–VCH; Weinheim: 2013

11a For a recent review on hypervalent iodine, see: Wang X, Studer A. Acc. Chem. Res. 2017; 50: 1712
11b For a recent review on applications in organic synthesis, see: Olding A, Ho CC. Aust. J. Chem. 2019; 72: 646
11c For a recent review on heterocycles synthesis, see: Takenaga N, China H, Kumar R, Dohi T. Heterocycles 2021; 103: 144

12 Huang X, Groves JT. ACS Catal. 2016; 6: 751
13 For the seminal work, see: Zhdankin VV, Krasutsky AP, Kuehl CJ, Simonsen AJ, Woodward JK, Mismash B, Bolz JT. J. Am. Chem. Soc. 1996; 118: 5192
14 Akai S, Okuno T, Egi M, Takada T, Tohma H, Kita Y. Heterocycles 1996; 42: 47
15 Matsumoto K, Nakajima M, Nemoto T. J. Phys. Org. Chem. 2019; 32: e3961
16 Yang X.-G, Du F.-H, Li J.-J, Zhang C. Chem. Eur. J. 2022; 28: e202200272
17 Alazet S, Preindl J, Simonet-Davin R, Nicolai S, Nanchen A, Meyer T, Waser J. J. Org. Chem. 2018; 83: 12334

18a Mironova IA, Kirsch SF, Zhdankin VV, Yoshimura A, Yusubov MS. Eur. J. Org. Chem. 2022; 2022: e202200754

This review also covers I(V) reagents, whereas we focus on I(III). For seminal examples of azidation using I(V) reagents, see:

18b Harschneck T, Hummel S, Kirsch SF, Klahn P. Chem. Eur. J. 2012; 18: 1187
18c Klahn P, Erhardt H, Kotthaus A, Kirsch SF. Angew. Chem. Int. Ed. 2014; 53: 7913

19a Zbiral E, Nestler G. Tetrahedron 1970; 26: 2945
19b Zbiral E, Ehrenfreund J. Tetrahedron 1971; 27: 4125
19c Ehrenfreund J, Zbiral E. Tetrahedron 1972; 28: 1697
19d Ehrenfreund J, Zbiral E. Justus Liebig Ann. Chem. 1973; (02) : 290
19e Moriarty RM, Khosrowshahi JS. Tetrahedron Lett. 1986; 27: 2809

20a Tingoli M, Tiecco M, Chianelli D, Balducci R, Temperini A. J. Org. Chem. 1991; 56: 6809
20b Fontana F, Minisci F, Yan YM, Zhao L. Tetrahedron Lett. 1993; 34: 2517

21 Magnus P, Lacour J, Weber W. J. Am. Chem. Soc. 1993; 115: 9347
22 Magnus P, Hulme C. Tetrahedron Lett. 1994; 35: 8097
23 Magnus P, Lacour J, Evans PA, Roe MB, Hulme C. J. Am. Chem. Soc. 1996; 118: 3406
24 Xie F, Qi Z, Li X. Angew. Chem. Int. Ed. 2013; 52: 11862
25 Matcha K, Narayan R, Antonchick AP. Angew. Chem. Int. Ed. 2013; 52: 7985
26 Nocquet-Thibault S, Rayar A, Retailleau P, Cariou K, Dodd RH. Chem. Eur. J. 2015; 21: 14205
27 Bosmani A, Pujari SA, Besnard C, Guénée L, Poblador-Bahamonde AI, Lacour J. Chem. Eur. J. 2017; 23: 8678
28 Chen W.-T, Gao L.-H, Bao W.-H, Wei W.-T. J. Org. Chem. 2018; 83: 11074
29 Li Z.-R, Wu D.-Q, Sun J, Shen J, Deng Q.-H. Asian J. Org. Chem. 2018; 7: 432
30 Wang X, Guo S, Zhang Y, Zhang Z, Zhang G, Ye Y, Sun K. Adv. Synth. Catal. 2021; 363: 3290
31 Gurawa A, Kumar M, Kashyap S. ACS Omega 2021; 6: 26623
32 Deng Q.-H, Bleith T, Wadepohl H, Gade LH. J. Am. Chem. Soc. 2013; 135: 5356
33 Vita MV, Waser J. Org. Lett. 2013; 15: 3246
34 Vita MV, Caramenti P, Waser J. Org. Lett. 2015; 17: 5832

35a Tiffner M, Stockhammer L, Schörgenhumer J, Röser K, Waser M. Molecules 2018; 23: 1142
35b Wang C.-J, Sun J, Zhou W, Xue J, Ren B.-T, Zhang G.-Y, Mei Y.-L, Deng Q.-H. Org. Lett. 2019; 21: 7315

36a Sharma A, Hartwig JF. Nature 2015; 517: 600
36b Karimov R, Sharma A, Hartwig JF. ACS Cent. Sci. 2016; 2: 715

37 Day CS, Fawcett A, Chatterjee R, Hartwig JF. J. Am. Chem. Soc. 2021; 143: 16184
38 Wang Y, Li G.-X, Yang G, Hea G, Chen G. Chem. Sci. 2016; 7: 2679
39 Rabet PT. G, Fumagalli G, Boyd S, Greaney MF. Org. Lett. 2016; 18: 1646
40 Shinomoto Y, Yoshimura A, Shimizu H, Yamazaki M, Zhdankin VV, Saito A. Org. Lett. 2015; 17: 5212
41 Huang L, Xun X, Zhao M, Xue J, Li G, Hong L. J. Org. Chem. 2019; 84: 11885
42 Allouche EM. D, Simonet-Davin R, Waser J. Chem. Eur. J. 2022; 28: e202200368
43 Zhang B, Studer A. Org. Lett. 2013; 15: 4548

44a Yin H, Wang T, Jiao N. Org. Lett. 2014; 16: 2302
44b Zhu L, Yu H, Xu Z, Jiang X, Lin L, Wang R. Org. Lett. 2014; 16: 1562

45 Kong W, Merino E, Nevado C. Angew. Chem. Int. Ed. 2014; 53: 5078
46 Kong W, Fuentes N, García-Domínguez A, Merino E, Nevado C. Angew. Chem. Int. Ed. 2015; 54: 2487
47 Fuentes N, Kong W, Fernández-Sánchez L, Merino E, Nevado C. J. Am. Chem. Soc. 2015; 137: 964
48 Li L, Li Z.-L, Wang F.-L, Guo Z, Cheng Y.-F, Wang N, Dong X.-W, Fang C, Liu J, Hou C, Tan B, Liu X.-Y. Nat. Commun. 2016; 7: 13852
49 Ouyang X.-H, Song R.-J, Liu Y, Hu M, Li J.-H. Org. Lett. 2015; 17: 6038
50 Li Z.-L, Li X.-H, Wang N, Yang N.-Y, Liu X.-Y. Angew. Chem. Int. Ed. 2016; 55: 15100
51 Li L, Gu Q.-S, Wang N, Song P, Li Z.-L, Li X.-H, Wang F.-L, Liu X.-Y. Chem. Commun. 2017; 53: 4038
52 Fumagalli G, Rabet PT. G, Boyd S, Greaney MF. Angew. Chem. Int. Ed. 2015; 54: 1148
53 Alazet S, Le Vaillant F, Nicolai S, Courant T, Waser J. Chem. Eur. J. 2017; 23: 9501
54 Shen K, Wang Q. J. Am. Chem. Soc. 2017; 139: 13110
55 Wang F.-L, Dong X.-Y, Lin J.-S, Zeng Y, Jiao G.-Y, Gu Q.-S, Guo X.-Q, Ma C.-L, Liu X.-Y. Chem 2017; 3: 979
56 Lonca GH, Ong DY, Tran TM. H, Tejo C, Chiba S, Gagosz F. Angew. Chem. Int. Ed. 2017; 56: 11440
57 500 mg of freshly prepared ABX (3) exploded while being handled with a spatula in a glass flask, resulting in several cuts and burns leading to the hospitalization of a postdoc, fortunately without long-term consequences.
58 Wu D, Cui S.-S, Lin Y, Li L, Yu W. J. Org. Chem. 2019; 84: 10978
59 Li X, Qi X, Hou C, Chen P, Liu G. Angew. Chem. Int. Ed. 2020; 59: 17239
60 Chen L, Xing H, Zhang H, Jiang Z.-X, Yang Z. Org. Biomol. Chem. 2016; 14: 7463
61 Bertho S, Rey-Rodriguez R, Colas C, Retailleau P, Gillaizeau I. Chem. Eur. J. 2017; 23: 17674
62 Jung H, Lim Y.-G. Polym. Chem. 2019; 10: 5348
63 Li M, Yu F, Chen P, Liu G. J. Org. Chem. 2017; 82: 11682
64 Cong F, Wei YL, Tang PP. Chem. Commun. 2018; 54: 4473
65 Liu D, Bielawski CW. Polym. Int. 2017; 66: 70
66 Shirke RP, Ramasastry SS. V. Org. Lett. 2017; 19: 5482
67 Li X, Chen P, Liu G. Sci. China Chem. 2019; 62: 1537
68 Li H, Shen S.-J, Zhu C.-L, Xu H. J. Am. Chem. Soc. 2019; 141: 9415
69 Zheng L, Wang Z, Li C, Wu Y, Liu Z, Ning Y. Chem. Commun. 2021; 57: 9874
70 Fan Y, Wan W, Ma G, Gao W, Jiang H, Zhu S, Hao J. Chem. Commun. 2014; 50: 5733
71 Hendrick CE, Bitting KJ, Cho S, Wang Q. J. Am. Chem. Soc. 2017; 139: 11622