Recent Advances and the Prospect of Hypervalent Iodine Chemistry

Xiao-Guang Yang; Ze-Nan Hu; Meng-Cheng Jia; Feng-Huan Du; Chi Zhang

doi:10.1055/a-1492-4943

Synlett, Table of Contents

Synlett 2021; 32(13): 1289-1296
DOI: 10.1055/a-1492-4943

cluster account

Perspectives on Organoheteroatom and Organometallic Chemistry

Recent Advances and the Prospect of Hypervalent Iodine Chemistry

Xiao-Guang Yang

,

Ze-Nan Hu

,

Meng-Cheng Jia

,

Feng-Huan Du

,

Chi Zhang∗

Abstract

All articles of this category

Dedicated to the College of Chemistry, Nankai University, on its 100^th anniversary

Abstract

Nowadays, hypervalent iodine chemistry has remarkably advanced in parallel with the emergence of novel hypervalent iodine reagents. Hypervalent iodine reagents, due to their outstanding characteristics including rich reactivities, excellent chemoselectivity, stability, and environmental friendliness, are becoming more and more popular in the synthetic organic chemistry. In this Account, a number of recent elegant research works and our perspective on the future of hypervalent iodine chemistry is presented.

1 Introduction

2 Recent Advances and Discussion

2.1 Novel Reactivities of Hypervalent Iodine Reagents

2.2 Atom-Economical Reactions Promoted by Hypervalent Iodine Reagents

2.3 Other Applications of Hypervalent Iodine Reagents

2.4 The Applications of DFT Calculations in Elucidating Reaction Mechanism Involving Hypervalent Iodine Reagents

3 Outlook and Conclusion

Key words

hypervalent iodine - oxidation - functional group transfer - atom economy - DFT calculation

Full Text

References

References and Notes
1 Zhdankin VV. Hypervalent Iodine Chemistry: Preparation, Structure and Synthetic Application of Polyvalent Iodine Compounds. John Wiley & Sons; New York: 2014

2a Yoshimura A, Zhdankin VV. Chem. Rev. 2016; 116: 3328
2b Li Y, Hari DP, Vita MV, Waser J. Angew. Chem. Int. Ed. 2016; 55: 4436
2c Wang X, Studer A. Acc. Chem. Res. 2017; 50: 1712

3 Willgerodt C. J. Prakt. Chem. 1886; 33: 154

For selected examples of the books, please see:

4a Varvoglis A. The Organic Chemistry of Polycoordinated Iodine. VCH Publishers; Weinheim: 1992
4b Varvoglis A. Hypervalent Iodine in Organic Synthesis. Academic Press; London: 1997
4c Wirth T. Top. Curr. Chem 2003; 1: 224

For selected examples of the reviews, please see:

5a Zhdankin VV, Stang PJ. Chem. Rev. 2008; 108: 5299
5b Merritt EA, Olofsson B. Angew. Chem. Int. Ed. 2009; 48: 9052
5c Dohi T, Kita Y. Chem. Commun. 2009; 2073
5d Singh FV, Wirth T. Chem. Asian J. 2014; 9: 950
5e Charpentier J, Früh N, Togni A. Chem. Rev. 2015; 115: 650
5f Duan Y.-N, Jiang S, Han Y.-C, Sun B, Zhang C. Chin. J. Org. Chem. 2016; 36: 3052
5g Han Y.-C, Zhang C. Tetrahedron Lett. 2018; 59: 3052
5h Hari DP, Caramenti P, Waser J. Acc. Chem. Res. 2018; 51: 3212
5i Murphy GK, Racicot L, Carle MS. Asian J. Org. Chem. 2018; 7: 837
5j Elsherbini M, Wirth T. Chem. Eur. J. 2018; 24: 13399
5k Parra A. Chem. Rev. 2019; 119: 12033
5l Ghosh MK, Rajkiewicz AA, Kalek M. Synthesis 2019; 51: 359

6 The data from https://scifinder.cas.org and ‘hypervalent iodine’ as the key word, January 2021.
7 The 7^th ICHIC in Moscow will be held in the summer of 2022: https://www.ichic2020.ru/index.php/en/.

For selected examples of the new hypervalent iodine reagents, please see:

8a Cui L.-Q, Dong Z.-L, Liu K, Zhang C. Org. Lett. 2011; 13: 6488
8b Harschneck T, Hummel S, Kirsch SF, Klahn P. Chem. Eur. J. 2012; 18: 1187
8c Souto A, Martínez C, Velilla I, Muñiz K. Angew. Chem. Int. Ed. 2013; 52: 1324
8d Yusubov MS, Svitich DY, Yoshimura A, Nemykin VN, Zhdankin VV. Chem. Commun. 2013; 49: 11269
8e Yang Y.-D, Azuma A, Tokunaga E, Yamasaki M, Shiro M, Shibata N. J. Am. Chem. Soc. 2013; 135: 8782
8f Garamenti P, Nicolai S, Waser J. Chem. Eur. J. 2017; 23: 14702
8g Xia H.-D, Zhang Y.-D, Wang Y.-H, Zhang C. Org. Lett. 2018; 20: 4052
8h Mészáros Á, Székely A, Stirling A, Novák Z. Angew. Chem. Int. Ed. 2018; 57: 6643
8i Kalim J, Duhail T, Le T.-N, Vanthuyne N, Anselmi E, Togni A, Magnier E. Chem. Sci. 2019; 10: 10516
8j Hokamp T, Wirth T. J. Org. Chem. 2019; 84: 8674
8k Yudasaka M, Shimbo D, Maruyama T, Tada N, Itoh A. Org. Lett. 2019; 21: 1098
8l Yusubov MS, Soldatova NS, Postnikov PS, Valiev RR, Yoshimura A, Wirth T, Nemykine VN, Zhdankin VV. Chem. Commun. 2019; 55: 7760
8m Ding W, Chai J, Wang C, Wu J, Yoshikai N. J. Am. Chem. Soc. 2020; 142: 8619
8n Zhang G.-T, Wang Y.-X, Xu J, Sun J.-Y, Sun F.-X, Zhang Y.-L, Zhang C.-L, Du Y.-F. Chem. Sci. 2020; 11: 947

For selected examples, please see:

9a Nicolaou KC, Zhong Y.-L, Baran PS. J. Am. Chem. Soc. 2000; 122: 7596
9b Nicolaou KC, Baran PS, Zhong Y.-L. J. Am. Chem. Soc. 2001; 123: 3183
9c Lee JC, Lee JY, Lee SJ. Tetrahedron Lett. 2004; 45: 4939
9d Zhao X.-F, Zhang C. Synthesis 2007; 551
9e Liu S.-S, Wang L, Duan Y.-N, Yu A, Zhang C. Sci. China Chem. 2019; 62: 597

10 Han D.-D, He Q.-Q, Fan R.-H. Nat. Commun. 2018; 9: 3423
11 Yu C, Patureau FW. Angew. Chem. Int. Ed. 2019; 58: 18530
12 Han Y.-C, Zhang Y.-D, Jia Q, Cui J, Zhang C. Org. Lett. 2017; 19: 5300
13 Xing B, Ni C, Hu J. Angew. Chem. Int. Ed. 2018; 57: 9896
14 Kiyokawa K, Okumatsu D, Minakata S. Angew. Chem. Int. Ed. 2019; 58: 8907
15 Yang X.-G, Zheng K, Zhang C. Org. Lett. 2020; 22: 2026
16 Okuyama T, Takino T, Sueda T, Ochiai M. J. Am. Chem. Soc. 1995; 117: 3360
17 Yoshimura A, Fuchs JM, Middleton KR, Maskaev AV, Rohde GT, Saito A, Postnikov PS, Yusubov MS, Nemykin VN, Zhdankin VV. Chem. Eur. J. 2017; 23: 16738
18 Silva FC. S, Van N T, Wengryniuk SE. J. Am. Chem. Soc. 2020; 142: 64
19 Tian J, Luo F, Zhang Q, Liang Y, Li D, Zhan Y, Kong L, Wang Z, Peng B. J. Am. Chem. Soc. 2020; 142: 6884
20 Wang M, Fan Q.-L, Jiang X.-F. Org. Lett. 2016; 18: 5756
21 Chen H, Han J, Wang L. Angew. Chem. Int. Ed. 2018; 57: 12313
22 Colomer I, Barcelos RC, Donohoe TJ. Angew. Chem. Int. Ed. 2016; 55: 4748
23 Juárez-Ornelas KA, Jiménez-Halla JO. C, Kato T, Solorio-Alvarado CR, Maruoka K. Org. Lett. 2019; 21: 1315
24 Zhao Z.-Z, Britt LH, Murphy GK. Chem. Eur. J. 2018; 24: 17002
25 Hashimoto T, Shimazaki Y, Omatsu Y, Maruoka K. Angew. Chem. Int. Ed. 2018; 57: 7200
26 He C, Hu J, Wu Y, Ding H. J. Am. Chem. Soc. 2017; 139: 6098
27 Li L, Yuan K, Jia Q.-L, Jia Y.-X. Angew. Chem. Int. Ed. 2019; 58: 6074
28 Abrecht S, Adam JM, Bromberger U, Diodone R, Fettes A, Fischer R, Goeckel V, Hildbrand S, Moine G, Weber M. Org. Process Res. Dev. 2011; 15: 503
29 Tian J, Gao W.-C, Zhou D.-M, Zhang C. Org. Lett. 2012; 14: 3020

30a Zhang C, Liu S.-S, Sun B, Tian J. Org. Lett. 2015; 17: 4106
30b Liu D, Guo Y.-L, Qu J, Zhang C. Beilstein J. Org. Chem. 2018; 14: 1112
30c Qiu L.-J, Liu D, Zheng K, Zhang M.-T, Zhang C. Front. Chem. 2020; 8: 183

31a Fokin AA, Schreiner PR. Adv. Synth. Catal. 2003; 345: 1035
31b Wang C, Liu F, Shi Z. Sci. Sin. Chim. 2020; 50: 756
31c Gunsalus NJ, Koppaka A, Park SH, Bischof SM, Hashiguchi BG, Periana RA. Chem. Rev. 2017; 117: 8521

32 Konnick MM, Hashiguchi BG, Devarajan D, Boaz NC, Gunnoe TB, Groves JT, Gunsalus N, Ess DH, Periana RA. Angew. Chem. Int. Ed. 2014; 53: 10490

For recent examples of DFT calculations in hypervalent iodine chemistry, please see:

33a Sajith PK, Suresh CH. Inorg. Chem. 2012; 51: 967
33b Zhou B, Yan T, Xue X.-S, Cheng J.-P. Org. Lett. 2016; 18: 6128
33c Jiang H, Sun T.-S, Wang X, Xie Y, Zhang X, Wu Y.-D, Schaefer HF. III. Org. Lett. 2017; 19: 6502
33d Zhou B, Haj MK, Jacobsen EN, Houk KN, Xue X.-S. J. Am. Chem. Soc. 2018; 140: 15206
33e Jiang H, Sun T.-Y, Chen Y, Zhang X, Wu Y.-D, Xie Y, Schaefer HF. III. Chem. Commun. 2019; 55: 5667
33f Farshadfar K, Chipman A, Yates BF, Ariafard A. ACS Catal. 2019; 9: 6510
33g Matsumoto K, Nakajima M, Nemoto T. J. Phys. Org. Chem. 2019; 32: 3961
33h Brea O, Szabó KJ, Himo F. J. Org. Chem. 2020; 85: 15577
33i Wang Q, Lübcke M, Biosca M, Hedberg M, Eriksson L, Himo F, Szabó KJ. J. Am. Chem. Soc. 2020; 142: 20048
33j Soldatova NS, Postnikov PS, Suslonov VV, Kissler TY, Ivanov DM, Yusubov MS, Galmés B, Frontera A, Kukushkin VY. Org. Chem. Front. 2020; 7: 2230
33k Farshadfar K, Bird MJ, Olivier WJ, Hyland CJ. T, Smith JA, Ariafard A. J. Org. Chem. 2021; 86: 2998