Pyrylium Salts: Selective Reagents for the Activation of Primary Amino Groups in Organic Synthesis

Yue Pang; Daniel Moser; Josep Cornella

doi:10.1055/s-0039-1690703

Synthesis, Table of Contents

Synthesis 2020; 52(04): 489-503
DOI: 10.1055/s-0039-1690703

short review

Pyrylium Salts: Selective Reagents for the Activation of Primary Amino Groups in Organic Synthesis

Yue Pang

^aDepartment of Organometallic Chemistry, Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470, Mülheim an der Ruhr, Germany Email: cornella@kofo.mpg.de

,

Daniel Moser

^aDepartment of Organometallic Chemistry, Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470, Mülheim an der Ruhr, Germany Email: cornella@kofo.mpg.de

^bCurrent address: University of Basel, Department of Chemistry, St. Johanns-Ring 19, 4056, Basel, Switzerland

,

Josep Cornella ∗

^aDepartment of Organometallic Chemistry, Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470, Mülheim an der Ruhr, Germany Email: cornella@kofo.mpg.de

› Author Affiliations

Abstract

All articles of this category

Published as part of the Bürgenstock Special Section 2019 Future Stars in Organic Chemistry

Abstract

Primary amino groups represent an ubiquitous category of functionalities in synthetic building blocks, drugs, and natural products. Therefore, such functionalities offer themselves as perfect handles for late-stage functionalization, and the development of robust and efficient strategies to transform these groups is highly desirable. Despite the extremely challenging activation of the C–N bond, the past few years have witnessed the rapid development of deaminative transformations using pyrylium salts as activating reagents. In most cases, the pyridinium salts formed were activated by single electron transfer, giving alkyl radicals which were used in a series of transformations via nickel and photoredox catalysis. This short review aims to give an overview to related properties of pyrylium salts, their historical significance, and summarize the recent progress in the field of deaminative transformations using these reagents.

1 Introduction

2 Pyrylium and Pyridinium Salts

2.1 Historical Context

2.2 Structure and Reactivity

2.3 Pyrylium Synthesis

2.4 Historical Context of the Reactivity of Pyridinium Salts

3 Recent Progress on Deaminative Transformations of Primary Amino Groups by Pyrylium Salts

3.1 Metal-Catalyzed Cross-Couplings

3.2 Photoredox Catalysis and Photoinduced Reactions for C–C Bond Constructions

3.3 Borylations

3.4 S_NAr Functionalization of Aminoheterocycles

4 Conclusion

Key words

pyrylium salts - primary amino groups - deaminative transformations - radical chemistry - nickel catalysis - photoredox catalysis

Full Text

References

References
1 Eastgate MD, Schmidt MA, Fandrick KR. Nat. Rev. Chem. 2017; 1: 0016
2 Homogeneous Catalysis for Unreactive Bond Activation. Shi Z.-J. Wiley-VCH; Weinheim: 2014

3a Ouyang K, Hao W, Zhang WX, Xi Z. Chem. Rev. 2015; 115: 12045
3b Wang Q, Su Y, Li L, Huang H. Chem. Soc. Rev. 2016; 45: 1257

4 Blanksby SJ, Ellison GB. Acc. Chem. Res. 2003; 36: 255

5a Amines: Synthesis, Properties and Applications . Lawrence SA. Cambridge University Press; Cambridge: 2004
5b Amino Group Chemistry: From Synthesis to the Life Sciences. Ricci A. Wiley-VCH; Weinheim: 2008

6a Mo F, Dong G, Zhang Y, Wang J. Org. Biomol. Chem. 2013; 11: 1582
6b He L, Qiu G, Gao Y, Wu J. Org. Biomol. Chem. 2014; 12: 6965
6c Wu G, Deng Y, Wu C, Zhang Y, Wang J. Angew. Chem. Int. Ed. 2014; 53: 10510

7a Blakey SB, MacMillan DW. C. J. Am. Chem. Soc. 2003; 125: 6046
7b Buszek KR, Brown N. Org. Lett. 2007; 9: 707
7c Maity P, Shacklady-McAtee DM, Yap GP. A, Sirianni ER, Watson MP. J. Am. Chem. Soc. 2013; 135: 280
7d Shacklady-McAtee DM, Roberts KM, Basch CH, Song Y.-G, Watson MP. Tetrahedron 2014; 70: 4257
7e Hu J, Sun H, Cai W, Pu X, Zhang Y, Shi Z. J. Org. Chem. 2016; 81: 14
7f Moragas T, Gaydou M, Martin R. Angew. Chem. Int. Ed. 2016; 55: 5053
7g Wang D.-Y, Yang Z.-K, Wang C, Zhang A, Uchiyama M. Angew. Chem. Int. Ed. 2018; 57: 3641
7h Rand AW, Montgomery J. Chem. Sci. 2019; 10: 5338

8a Tobisu M, Nakamura K, Chatani N. J. Am. Chem. Soc. 2014; 136: 5587
8b Wang S.-E, Wang L, He Q, Fan R. Angew. Chem. Int. Ed. 2015; 54: 13655
8c Cong X, Fan F, Ma P, Luo M, Chen H, Zeng X. J. Am. Chem. Soc. 2017; 139: 15182
8d Han D, He Q, Fan R. Nat. Commun. 2018; 9: 3423
8e Zhang Z, Zheng D, Wan Y, Zhang G, Bi J, Liu Q, Liu T, Shi L. J. Org. Chem. 2018; 83: 1369
8f Cao Z.-C, Li X.-L, Luo Q.-Y, Fang H, Shi Z.-J. Org. Lett. 2018; 20: 1995
8g Zhang Z.-B, Ji C.-L, Yang C, Chen J, Hong X, Xia J.-B. Org. Lett. 2019; 21: 1226

9a Katritzky AR. Tetrahedron 1980; 36: 679
9b Katritzky AR, Marson CM. Angew. Chem. Int. Ed. 1984; 23: 420
9c Balaban, A. T. 2,4,6-Triphenylpyrylium Tetrafluoroborate, In e-EROS Encyclopedia of Reagents for Organic Synthesis [Online]; Wiley & Sons, Posted October 15, 2005; DOI: 10.1002/047084289X.rn00618.

10a Kong D, Moon PJ, Lundgren RJ. Nat. Catal. 2019; 2: 473
10b He F.-S, Ye S, Wu J. ACS Catal. 2019; 9: 8943

11 von Kostanecki S, Rossbach G. Ber. Dtsch. Chem. Ges. 1896; 29: 1488
12 Dilthey W. J. Prakt. Chem. 1916; 94: 53
13 Grigor’ev VP, Ekilik VV. Zh. Prikl. Khim. 1969; 41
14 Bawn CE. H, Carruthers R, Ledwith A. J. Chem. Soc., Chem. Commun. 1965; 522
15 Rulliere C, Declemy A, Balaban AT. Can. J. Phys. 1985; 63: 191
16 Hartmann H, Förster D. J. Prakt. Chem. 1971; 313

17a Pyrylium Salts: Syntheses, Reactions and Physical Properties, Vol. 2. Balaban AT, Dinculescu A, Dorofeenko GN, Fischer GW, Koblik AV, Mezheritskii VV, Schroth W. Academic Press; 1982
17b Balaban TS, Balaban AT. Pyrylium Salts . In Science of Synthesis, Vol. 15. Georg Thieme Verlag; Stuttgart: 2004: 11-200

18a Dimroth K. Angew. Chem. 1960; 72: 331
18b Dulenko VI, Tolkunov SV. Chem. Heterocycl. Compd. 1987; 23: 730

19 Belosludtsev YY, Borer BC, Taylor RJ. K. Synthesis 1991; 320
20 Miranda MA, Garcia H. Chem. Rev. 1994; 94: 1063
21 Romero NA, Nicewicz DA. Chem. Rev. 2016; 116: 10075

22a Farid S, Shealer SE. J. Chem. Soc., Chem. Commun. 1973; 677
22b Martiny M, Steckhan E, Esch T. Chem. Ber. 1993; 126: 1671
22c Riener M, Nicewicz DA. Chem. Sci. 2013; 4: 2625

23a Wiest O, Steckhan E. Angew. Chem. Int. Ed. 1993; 32: 901
23b Perkowski AJ, Cruz CL, Nicewicz DA. J. Am. Chem. Soc. 2015; 137: 15684

24 Akaba R, Sakuragi H, Tokumaru K. J. Chem. Soc., Perkin Trans. 2 1991; 291
25 Akaba R, Niimura Y, Fukushima T, Kawai Y, Tajima T, Kuragami T, Negishi A, Kamata M, Sakuragi H, Tokumaru K. J. Am. Chem. Soc. 1992; 114: 4460

26a Bird CW. Tetrahedron 1986; 42: 89
26b Omelchenko IV, Shishkin OV, Gorb L, Leszczynski J, Fias S, Bultinck P. Phys. Chem. Chem. Phys. 2011; 13: 20536

27 Spitzner R, Radeglia R, Schroth W. Tetrahedron Lett. 1985; 26: 3967
28 Van der Plas HC. Acc. Chem. Res. 1978; 11: 462
29 Dimroth K, Berndt A, Reichardt C. Org. Synth., Coll. Vol. 5 . John Wiley & Sons; London: 1973: 1128

30a Wizinger R, Ulrich P. Helv. Chim. Acta 1956; 39: 207
30b Reynolds GA. Synthesis 1975; 638

31a Märkl G. Angew. Chem. Int. Ed. 1966; 5: 846
31b Breit B. Chem. Commun. 1996; 2071
31c Müller C, Vogt D. Dalton Trans. 2007; 5505

32a Katritzky AR, Lloyd JM, Patel RC. Chem. Scr. 1981; 18: 256
32b Katritzky AR, Leahy DE. J. Chem. Soc., Perkin Trans. 2 1985; 171

33 Dimroth K, Reichardt C, Vogel K. Org. Synth., Coll. Vol. 5 . John Wiley & Sons; London: 1973: 1135
34 Bos HJ. T, Arens JF. Recl. Trav. Chim. Pays-Bas 1963; 82: 845

35a Lombard R, Stephan JP. Bull. Soc. Chem. Fr. 1957; 1369
35b Lombard R, Stephan JP. Bull. Soc. Chem. Fr. 1958; 1458

36 VanAllan JA, Reynolds GA. J. Org. Chem. 1968; 33: 1102
37 Alfonzo E, Alfonso FS, Beeler AB. Org. Lett. 2017; 19: 2989

38a Strating J, Keijer JH, Molenaar E, Brandsma L. Angew. Chem. Int. Ed. 1962; 1: 399
38b Dimroth K, Kinzebach W, Soyka M. Chem. Ber. 1966; 99: 2351
38c Greulich TW, Daniliuc CG, Studer A. Org. Lett. 2015; 17: 254

39a Becher J. Org. Synth. 1979; 59: 79
39b Moser D, Duan Y, Wang F, Ma Y, O’Neill MJ, Cornella J. Angew. Chem. Int. Ed. 2018; 57: 11035

40 Milov AA, Starikov AG, Gridin MK, Minyaev RM. Russ. J. Gen. Chem. 2007; 77: 1373

41a Katritzky AR, Thind SS. J. Chem. Soc., Perkin Trans. 1 1980; 1895
41b Katritzky AR, Lloyd JM, Patel RC. J. Chem. Soc., Perkin Trans. 1 1982; 117

42a Eweiss NF, Katritzky AR, Nie P.-L, Ramsden CA. Synthesis 1977; 634
42b Katritzky AR, Gruntz U, Mongelli N, Rezende MC. J. Chem. Soc., Chem. Commun. 1978; 133
42c Katritzky AR, Bapat JB, Blade RJ, Leddy BP, Nie P.-L, Ramsden CA, Thind SS. J. Chem. Soc., Perkin Trans. 1 1979; 418
42d Katritzky AR, Chermprapai A, Patel RC. J. Chem. Soc., Chem. Commun. 1979; 238
42e Katritzky AR, Gruntz U, Ikizler AA, Kenny DH, Leddy BP. J. Chem. Soc., Perkin Trans. 1 1979; 436
42f Katritzky AR, Gruntz U, Kenny DH, Rezende MC, Sheikh H. J. Chem. Soc., Perkin Trans. 1 1979; 430
42g Katritzky AR, Lewis J, Nie P.-L. J. Chem. Soc., Perkin Trans. 1 1979; 442
42h Katritzky AR, Liso G, Lunt E, Patel RC, Thind SS, Zia A. J. Chem. Soc., Perkin Trans. 1 1980; 849
42i Katritzky AR, Marzorati L. J. Org. Chem. 1980; 45: 2515
42j Katritzky AR, Saba A, Patel RC. J. Chem. Soc., Perkin Trans. 1 1981; 1492
42k Katritzky AR, Akram Kashmiri M, Wittmann DK. Tetrahedron 1984; 40: 1501

43a Katritzky AR, Musumarra G. Chem. Soc. Rev. 1984; 13: 47
43b Katritzky AR, de Ville GZ, Patel RC. Tetrahedron Lett. 1980; 21: 1723

44a Katritzky AR, Eweiss NF, Nie P.-L. J. Chem. Soc., Perkin Trans. 1 1979; 433
44b Katritzky AR, Thind SS. J. Chem. Soc., Perkin Trans. 1 1980; 865
44c Katritzky AR, Cozens AJ. J. Chem. Soc., Perkin Trans. 1 1983; 2611
44d Katritzky AR, Wittmann DK, Chen J.-L, Marson CM, Ossana A. J. Heterocycl. Chem. 1986; 23: 865

45 Yan M, Lo JC, Edwards JT, Baran PS. J. Am. Chem. Soc. 2016; 138: 12692

46a Levin MD, Kim S, Toste FD. ACS Cent. Sci. 2016; 2: 293
46b Twilton J, Le C, Zhang P, Shaw MH, Evans RW, MacMillan DW. C. Nat. Rev. Chem. 2017; 1: 0052

47a Choi J, Fu GC. Science 2017; 356: 7230
47b Tasker SZ, Standley EA, Jamison TF. Nature 2014; 509: 299

48 Prier CK, Rankic DA, MacMillan DW. Chem. Rev. 2013; 113: 5322

49a Zuo Z, Ahneman DT, Chu L, Terrett JA, Doyle AG, MacMillan DW. C. Science 2014; 345: 437
49b Qin T, Cornella J, Li C, Malins LR, Edwards JT, Kawamura S, Maxwell BD, Eastgate MD, Baran PS. Science 2016; 352: 801

50a Nawrat CC, Jamison CR, Slutskyy Y, MacMillan DW. C, Overman LE. J. Am. Chem. Soc. 2015; 137: 11270
50b Zhang X, MacMillan DW. C. J. Am. Chem. Soc. 2016; 138: 13862

51 Basch CH, Liao J, Xu J, Piane JJ, Watson MP. J. Am. Chem. Soc. 2017; 139: 5313

52a Liao J, Guan W, Boscoe BP, Tucker JW, Tomlin JW, Garnsey MR, Watson MP. Org. Lett. 2018; 20: 3030
52b Guan W, Liao J, Watson MP. Synthesis 2018; 50: 3231

53 Plunkett S, Basch CH, Santana SO, Watson MP. J. Am. Chem. Soc. 2019; 141: 2257

54a Weix DJ. Acc. Chem. Res. 2015; 48: 1767
54b Gu J, Wang X, Xue W, Gong H. Org. Chem. Front. 2015; 2: 1411

55a Ni S, Li C.-X, Mao Y, Han J, Wang Y, Yan H, Pan Y. Sci. Adv. 2019; 5: 9516
55b Yue H, Zhu C, Shen L, Geng Q, Hock KJ, Yuan T, Cavallo L, Rueping M. Chem. Sci. 2019; 10: 4430
55c Liao J, Basch CH, Hoerrner ME, Talley MR, Boscoe BP, Tucker JW, Garnsey MR, Watson MP. Org. Lett. 2019; 21: 2941
55d Martin-Montero R, Yatham VR, Yin H, Davies J, Martin R. Org. Lett. 2019; 21: 2947
55e Yi J, Badir SO, Kammer LM, Ribagorda M, Molander GA. Org. Lett. 2019; 21: 3346

56 Hoerrner ME, Baker KM, Basch CH, Bampo EM, Watson MP. Org. Lett. 2019; 21: 7356
57 Li C.-L, Jiang X, Lu L.-Q, Xiao W.-J, Wu X.-F. Org. Lett. 2019; 21: 6919
58 Minisci F, Fontana F, Vismara E. J. Heterocycl. Chem. 1990; 27: 79
59 Klauck FJ. R, James MJ, Glorius F. Angew. Chem. Int. Ed. 2017; 56: 12336
60 Ociepa M, Turkowska J, Gryko D. ACS Catal. 2018; 8: 11362
61 Zhang MM, Liu F. Org. Chem. Front. 2018; 5: 3443
62 Wu J, Grant PS, Li X, Noble A, Aggarwal VK. Angew. Chem. Int. Ed. 2019; 58: 5697
63 Cabri W, Candiani I. Acc. Chem. Res. 1995; 28: 2

64a Ikeda Y, Nakamura T, Yorimitsu H, Oshima K. J. Am. Chem. Soc. 2002; 124: 6514
64b Zhu N, Zhao J, Bao H. Chem. Sci. 2017; 8: 2081

65 Jiang X, Zhang MM, Xiong W, Lu LQ, Xiao WJ. Angew. Chem. Int. Ed. 2019; 58: 2402
66 Yang ZK, Xu NX, Wang C, Uchiyama M. Chem. Eur. J. 2019; 25: 5433
67 Schweitzer-Chaput B, Horwitz MA, de Pedro Beato E, Melchiorre P. Nat. Chem. 2019; 11: 129
68 Fu M.-C, Shang R, Zhao B, Wang B, Fu Y. Science 2019; 363: 1429
69 James MJ, Strieth-Kalthoff F, Sandfort F, Klauck FJ. R, Wagener F, Glorius F. Chem. Eur. J. 2019; 25: 8240
70 Klauck FJ. R, Yoon H, James MJ, Lautens M, Glorius F. ACS Catal. 2019; 9: 236
71 Zhu ZF, Zhang MM, Liu F. Org. Biomol. Chem. 2019; 17: 1531
72 Fyfe JW. B, Watson AJ. B. Chem 2017; 3: 31

73a Candish L, Teders M, Glorius F. J. Am. Chem. Soc. 2017; 139: 7440
73b Fawcett A, Pradeilles J, Wang Y, Mutsuga T, Myers EL, Aggarwal VK. Science 2017; 357: 283

74a Li C, Wang J, Barton LM, Yu S, Tian M, Peters DS, Kumar M, Yu AW, Johnson KA, Chatterjee AK, Yan M, Baran PS. Science 2017; 356: 7355
74b Hu D, Wang L, Li P. Org. Lett. 2017; 19: 2770

75 Wu J, He L, Noble A, Aggarwal VK. J. Am. Chem. Soc. 2018; 140: 10700
76 Sandfort F, Strieth-Kalthoff F, Klauck FJ. R, James MJ, Glorius F. Chem. Eur. J. 2018; 24: 17210
77 Hu J, Wang G, Li S, Shi Z. Angew. Chem. Int. Ed. 2018; 57: 15227

78a Schneider N, Lowe DM, Sayle RA, Tarselli MA, Landrum GA. J. Med. Chem. 2016; 59: 4385
78b Brown DG, Boström J. J. Med. Chem. 2016; 59: 4443