Heteroatom-Embedding Annulative π-Extension (Hetero-APEX) Reactions: An Overview

Hideto Ito; Kou P. Kawahara; Kenichiro Itami

doi:10.1055/a-2169-4078

Synthesis, Table of Contents

Synthesis 2024; 56(09): 1335-1354
DOI: 10.1055/a-2169-4078

review

Heteroatom-Embedding Annulative π-Extension (Hetero-APEX) Reactions: An Overview

Hideto Ito ∗

^aGraduate School of Science, Nagoya University, Chikusa, Nagoya 464-8602, Japan

,

Kou P. Kawahara

^aGraduate School of Science, Nagoya University, Chikusa, Nagoya 464-8602, Japan

,

Kenichiro Itami ∗

^aGraduate School of Science, Nagoya University, Chikusa, Nagoya 464-8602, Japan

^bInstitute of Transformative Bio-Molecules (WPI-ITbM), Nagoya University, Chikusa, Nagoya 464-8602, Japan

› Author Affiliations

Abstract

All articles of this category

Abstract

Heteroatom-embedded polycyclic aromatic compounds (hetero-PACs) are a class of organic compounds contributing to a variety of research fields such as materials science, chemical biology, and so on. For applications using hetero-PACs, efficient preparation of hetero-PACs is essential. In particular, reactions transforming unfunctionalized aromatic compounds into hetero-PACs using appropriate heteroatom-containing aromatic compounds (π-extending agents) represent the most ideal way to prepare hetero-PACs. In this review, such heteroatom-embedding annulative π-extension (hetero-APEX) reactions, including their reaction mechanisms and scope of substrates, are described.

1 Introduction

2 Oxa-APEX Reactions

3 Aza-APEX Reactions

4 Thia-APEX Reactions

5 Conclusion and Outlook

Key words

annulative π-extension - polycyclic aromatic compounds - annulation - heteroaromatics - π-extended compounds - heteroles

Full Text

References

References

1a Stępień M, Gońka E, Żyła M, Sprutta N. Chem. Rev. 2017; 117: 3479
1b Borissov A, Maurya YK, Moshniaha L, Wong W.-S, Żyła-Karwowska M, Stępień M. Chem. Rev. 2022; 122: 565
1c Li H, Shi W, Song J, Jang H.-J, Dailey J, Yu J, Katz HE. Chem. Rev. 2019; 119: 3
1d Karak P, Rana SS, Choudhury J. Chem. Commun. 2022; 58: 133
1e Wang C, Dong H, Hu W, Liu Y, Zhu D. Chem. Rev. 2012; 112: 2208
1f Janosik T, Rannug A, Rannug U, Wahlström N, Slatt J, Bergman J. Chem. Rev. 2018; 118: 9058
1g Hirai M, Tanaka N, Sakai M, Yamaguchi S. Chem. Rev. 2019; 119: 8291
1h Dhbaibi K, Favereau L, Crassous J. Chem. Rev. 2019; 119: 884
1i Wöhrle T, Wurzbach I, Kirres J, Kostidou A, Kapernaum N, Litterscheidt J, Haenle JC, Staffeld P, Baro A, Giesselmann F, Laschat S. Chem. Rev. 2016; 116: 1139
1j Cai Z, Awais MA, Zhang N, Yu L. Chem 2018; 4: 2538
1k Anthony JE. Chem. Rev. 2006; 106: 5028

2a Terrones H, Lv R, Terrones M, Dresselhaus MS. Rep. Prog. Phys. 2012; 75: 062501
2b Szűcs R, Bouit P.-A, Nyulászi L, Hissler M. ChemPhysChem 2017; 18: 2618
2c Jeong E.-J, Kim Y.-K, Park J.-H, Lee E.-Y, Hwang S.-H. US 20150349275A1, 2015
2d Nakayama K, Hashimoto Y, Sasabe H, Pu Y.-J, Yokoyama M, Kido J. Jpn. J. Appl. Phys. 2010; 49: 01AB11
2e Yamaguchi AD, Chepiga KM, Yamaguchi J, Itami K, Davies HM. L. J. Am. Chem. Soc. 2015; 137: 644
2f Ma Y, Sun Y, Liu Y, Gao J, Chen S, Sun X, Qiu W, Yu G, Cui G, Hu W, Zhu D. J. Mater. Chem. 2005; 15: 4894
2g Bazzini C, Brovelli S, Caronna T, Gambarotti C, Giannone M, Macchi P, Meinardi F, Mele A, Panzeri W, Recupero F, Sironi A, Tubino R. Eur. J. Org. Chem. 2005; 1247
2h Xiao L, Lan H, Kido J. Chem. Lett. 2007; 36: 802
2i Cheng C.-H, Wu J.-L, Liao C.-Y. US 8753756B2, 2014
2j Mamada M, Minamiki T, Katagiri H, Tokito S. Org. Lett. 2012; 14: 4062
2k Tanaka K, Iwama Y, Kishimoto M, Ohtsuka N, Hoshino Y, Honda K. Org. Lett. 2020; 22: 5207
2l Li M, Xie W, Cai X, Peng X, Liu K, Gu Q, Zhou J, Qiu W, Chen Z, Gan Y, Su S.-J. Angew. Chem. Int. Ed. 2022; 61: e202209343
2m Tsuji H, Nakamura E. Acc. Chem. Res. 2017; 50: 396
2n Chen X, Yan L, Liu Y, Yang Y, You J. Chem. Commun. 2020; 56: 15080

3a Marco-Contelles J, Pérez-Mayoral E, Samadi A, Carreiras M. dC, Soriano E. Chem. Rev. 2009; 109: 2652
3b Sun Y.-X, Wang X.-G, Shen G.-D, Yang T, Yang Y.-H, Li J, Yang M.-Y, Sun H.-M, Wei J.-F. Adv. Synth. Catal. 2020; 362: 1651
3c Goujon A, Rocard L, Cauchy T, Hudhomme P. J. Org. Chem. 2020; 85: 7218
3d Strekowski L, Czarny A, Lee H. J. Fluorine Chem. 2000; 104: 281
3e Tsvelikhovsky D, Buchwald SL. J. Am. Chem. Soc. 2010; 132: 14048
3f Ye X, Xu B, Sun J, Dai L, Shao Y, Zhang Y, Chen J. J. Org. Chem. 2020; 85: 13004
3g Wang T.-J, Chen W.-W, Lia Y, Xu M.-H. Org. Biomol. Chem. 2015; 13: 6580
3h Pang X, Lou Z, Li M, Wen L, Chen C. Eur. J. Org. Chem. 2015; 3361
3i Guo H.-M, Mao R.-Z, Wang Q.-T, Niu H.-Y, Xie M.-S, Qu G.-R. Org. Lett. 2013; 15: 5460

Examples of construction of pyrylium/thiopyrylium structures:

4a Kharchenko VG, Kleimenova VI, Yakoreva AR. Chem. Heterocycl. Compd. 1970; 6: 834
4b Berényi S, Tóth M, Gyulai S, Szilágyi L. Heterocycles 2002; 57: 135
4c Wu D, Pisula W, Haberecht MC, Feng X, Müllen K. Org. Lett. 2009; 11: 5686
4d Nagahora N, Kushida T, Shioji K, Okuma K. Organometallics 2019; 38: 1800
4e Tanaka K, Kishimoto M, Sukekawa M, Hoshino Y, Honda K. Tetrahedron Lett. 2018; 59: 3361
4f Shen G.-B, Xia K, Li X.-T, Li J.-L, Fu Y.-H, Yuan L, Zhu X.-Q. J. Phys. Chem. A 2016; 120: 1779
4g Shenbor MI, Azarov AS. Khim. Getero. Soedin. 1979; 29
4h Rao KP, Kusamoto T, Toshimitsu F, Inayoshi K, Kume S, Sakamoto R, Nishihara H. J. Am. Chem. Soc. 2010; 132: 12472
4i Wehrmann CM, Charlton RT, Chen MS. J. Am. Chem. Soc. 2019; 141: 3240
4j Spiliopoulos IK, Mikroyannidis JA. Macromolecules 2002; 35: 7254

5 Lv B, Xiao J, Zhou J, Zhang X, Duan J, Su W, Zhao J. ACS Appl. Mater. Interfaces 2016; 8: 18998
6 Saint-Ruf G, Buu-Hoï NP, Jacquignon P. J. Chem. Soc. 1958; 1773
7 Zhang S, Qiao X, Chen Y, Wang Y, Edkins RM, Liu Z, Li H, Fang Q. Org. Lett. 2014; 16: 342

8a Mackey K, Jones DJ, Pardo LM, McGlacken GP. Eur. J. Org. Chem. 2021; 495
8b Đorđević L, Milano D, Demitri N, Bonifazi D. Org. Lett. 2020; 22: 4283

Other examples of constructing heteroaromatic rings:

9a Waley MW, Gorindachari TR. Org. React. 1951; 6: 74
9b Imran M, Wehrmann CM, Chen MS. J. Am. Chem. Soc. 2020; 142: 38
9c Greßies S, Ito M, Sakai M, Osaki H, Kim JH, Gensch T, Daniliuc C, Ando N, Yamaguchi S, Glorius F. Chem. Eur. J. 2021; 27: 2753
9d Larock RC, Yum EK, Refvik MD. J. Org. Chem. 1998; 63: 7652
9e Masuya Y, Tobisu M, Chatani N. Org. Lett. 2016; 18: 4312
9f Zeng W, Wu W, Jiang H, Huang L, Sun Y, Chen Z, Li X. Chem. Commun. 2013; 49: 6611
9g Wang S, Lv B, Cui Q, Ma X, Ba X, Xiao J. Chem. Eur. J. 2015; 21: 14791
9h Yue D, Larock RC. J. Org. Chem. 2002; 67: 1905
9i Meng L, Fujikawa T, Kuwayama M, Segawa Y, Itami K. J. Am. Chem. Soc. 2016; 138: 10351
9j Song T, Han Y, Jin P, Li X, Song Y, Xiao J. J. Mater. Chem. C 2019; 7: 6344
9k Miletić T, Fermi A, Orfanos I, Avramopoulos A, De Leo F, Demitri N, Bergamini G, Ceroni P, Papadopoulos MG, Couris S, Bonifazi D. Chem. Eur. J. 2017; 23: 2363
9l Saha M, Bao Y.-H, Zhou CA. Chem. Lett. 2018; 47: 1383
9m Ma Y, Shi Z, Zhang A, Li J, Wei X, Jiang T, Li Y, Wang X. Dyes Pigm. 2016; 135: 41

10a Ito H, Ozaki K, Itami K. Angew. Chem. Int. Ed. 2017; 56: 11144
10b Ito H, Segawa Y, Murakami K, Itami K. J. Am. Chem. Soc. 2019; 141: 3

Representative examples of APEX reaction of PAH and heteroaromatics:

11a Ozaki K, Zhang H, Ito H, Lei A, Itami K. Chem. Sci. 2013; 4: 3416
11b Ozaki K, Kawasumi K, Shibata M, Ito H, Itami K. Nat. Commun. 2015; 6: 6251
11c Ozaki K, Matsuoka W, Ito H, Itami K. Org. Lett. 2017; 19: 1930
11d Matsuoka W, Ito H, Itami K. Angew. Chem. Int. Ed. 2017; 56: 12224
11e Kitano H, Matsuoka W, Ito H, Itami K. Chem. Sci. 2018; 9: 7556
11f Nakamuro T, Kumazawa K, Ito H, Itami K. Synlett 2019; 30: 423
11g Matsuoka W, Ito H, Sarlah D, Itami K. Nat. Commun. 2021; 12: 3940
11h Matsuoka W, Kawahara KP, Ito H, Sarlah D, Itami K. J. Am. Chem. Soc. 2023; 145: 658
11i Kawahara KP, Matsuoka W, Ito H, Itami K. Angew. Chem. Int. Ed. 2020; 59: 6383

12 Shibata M, Ito H, Itami K. J. Am. Chem. Soc. 2018; 140: 2196

Examples of APEX reactions reported by other groups:

13a Schuler B, Collazos S, Gross L, Meyer G, Pérez D, Guitián E, Peña D. Angew. Chem. Int. Ed. 2014; 53: 9004
13b Sakakibara T, Tanaka Y, Yamaki S. Chem. Lett. 1986; 15: 797
13c Pham VM, Cramer N. Angew. Chem. Int. Ed. 2014; 53: 3484
13d Abid M, Spaeth A, Török B. Adv. Synth. Catal. 2006; 348: 2191
13e Dann O, Kokorudz M, Gropper R. Chem. Ber. 1954; 87: 140
13f Tang R.-Y, Li J.-H. Chem. Eur. J. 2010; 16: 4733
13g Clement JA, Sivasakthikumaran R, Mohanakrishnan AK, Sundaramoorthy S, Velmurugan D. Eur. J. Org. Chem. 2011; 569
13h Deb ML, Baruah B, Bhuyan PJ. Synthesis 2008; 286
13i Alonso M. Á, López-Alvarado P, Avendaño C, Menéndez JC. Tetrahedron 2003; 59: 2821
13j Laha JK, Dayal N. Org. Lett. 2015; 17: 4742
13k Matsuda Y, Naoe S, Oishi S, Fujii N, Ohno H. Chem. Eur. J. 2015; 21: 1463
13l Yamashita M, Horiguchi H, Hirano K, Satoh T, Miura M. J. Org. Chem. 2009; 74: 7481
13m Song G, Gong X, Li X. J. Org. Chem. 2011; 76: 7583
13n Lee JB, Kim GH, Jeon JH, Jeong SY, Lee S, Park J, Lee D, Kwon Y, Seo JK, Chun J.-H, Kang SJ, Choe W, Rohde J.-U, Hong SY. Nat. Commun. 2022; 13: 2421
13o Fort EH, Scott LT. Angew. Chem. Int. Ed. 2010; 49: 6626
13p Clar E, Zander M. J. Chem. Soc. 1957; 4616
13q Li J, Jiao C, Huang K.-W, Wu J. Chem. Eur. J. 2011; 17: 14672
13r Konishi A, Hirao Y, Matsumoto K, Kurata H, Kubo T. Chem. Lett. 2013; 42: 592

14a Ito S, Itoh T, Nakamura M. Angew. Chem. Int. Ed. 2011; 50: 454
14b Matsumoto A, Ilies L, Nakamura E. J. Am. Chem. Soc. 2011; 133: 6557

15 Musgrave OC, Webster CJ. J. Chem. Soc., Perkin Trans. 1 1974; 2260
16 Morrison BJ, Musgrave OC. J. Chem. Res. 2005; 2005: 549
17 Qarah A, Gasonoo M, Do D, Klumpp DA. Tetrahedron Lett. 2016; 57: 3711
18 Bashir MA, Zhang Y, Yu H, Wang B, Zhao W, Zhong F. Green Chem. 2021; 23: 5031

19a Tan G, You Q, Lan J, You J. Angew. Chem. Int. Ed. 2018; 57: 6309
19b Wang Z, Yang M, Yang Y. Org. Lett. 2018; 20: 3001

20a Zhang F.-G, Chen Z, Tang X, Ma J.-A. Chem. Rev. 2021; 121: 14555
20b Takahashi M, Ishida H, Kohmoto M. Bull. Chem. Soc. Jpn. 1976; 49: 1725
20c Benson SC, Palabrica CA, Snyder JK. J. Org. Chem. 1987; 52: 4610

21a Benson SC, Gross JL, Snyder JK. J. Org. Chem. 1990; 55: 3257
21b Wan Z, Snyder JK. Tetrahedron Lett. 1997; 38: 7495
21c Lahue BR, Wan Z.-K, Snyder JK. J. Org. Chem. 2003; 68: 4345
21d Benson SC, Li J.-H, Snyder JK. J. Org. Chem. 1992; 57: 5285

22 Hiruta K, Kitahara K, Nishi H, Tokita S. Synthesis 1982; 229
23 Aksenov AV, Aksenov NA, Lyakhovnenko AS, Aksenova IV. Synthesis 2009; 3439

24a Tokimaru Y, Ito S, Nozaki K. Angew. Chem. Int. Ed. 2018; 57: 9818
24b Tokimaru Y, Ito S, Nozaki K. Angew. Chem. Int. Ed. 2017; 56: 15560
24c Zhang X, Mackinnon MR, Bodwell GJ, Ito S. Angew. Chem. Int. Ed. 2022; 61: e202116585

For reviews, see:

25a Bodwell GJ, Venkataramana G, Sagar UK. In Fragments of Fullerenes and Carbon Nanotubes: Designed Synthesis, Unusual Reactions, and Coordination Chemistry. Petrukhina MA, Scott LT. Wiley; Hoboken: 2011: 367
25b Bodwell GJ. Chem. Rec. 2014; 14: 547

26 Maiti S, Achar TK, Mal P. Org. Lett. 2017; 19: 2006

27a Gassner C, Hesse R, Schmidt AW, Knolker H.-J. Org. Biomol. Chem. 2014; 12: 6490
27b Cho SH, Yoon J, Chang S. J. Am. Chem. Soc. 2011; 133: 5996
27c Krahl MP, Jager A, Krause T, Knolker H.-J. Org. Biomol. Chem. 2006; 4: 3215

28 Regar R, Mishra R, Mondal PK, Sankar J. J. Org. Chem. 2018; 83: 9547
29 Wang M, Kong L, Wang F, Li X. Adv. Synth. Catal. 2017; 359: 4411
30 Schendera E, Unkel L.-N, Quyen PP. H, Salkewitz G, Hoffmann F, Villinger A, Brasholz M. Chem. Eur. J. 2020; 26: 269
31 Kouznetsov VV. Tetrahedron 2009; 65: 2721
32 Yu Z, Zhang Y, Tang J, Zhang L, Liu Q, Li Q, Gao G, You J. ACS Catal. 2020; 10: 203
33 Chen C, Wang Y, Shi X, Sun W, Zhao J, Zhu Y.-P, Liu L, Zhu B. Org. Lett. 2020; 22: 4097
34 Klemm LH, Lawrence RF. J. Heterocycl. Chem. 1979; 16: 599

35a Neugebauer W, Kos AJ, Schleyer P. vR. J. Organomet. Chem. 1982; 228: 107
35b Ashe AJ, Kampf JW, Savla PM. J. Org. Chem. 1990; 55: 5558
35c Ashe AJ, Kampf JW, Savla PM. Heteroat. Chem. 1994; 5: 113
35d Chintala SM, Petroff JT, Barnes A, McCulla RD. J. Sulfur Chem. 2019; 40: 503
35e Philipp S, Dominik J, Arne B. WO 2012048781A1, 2012
35f Furukawa S, Suda Y, Kobayashi J, Kawashima T, Tada T, Fujii S, Kiguchi M, Saito M. J. Am. Chem. Soc. 2017; 139: 5787

36 Yan J, Pulis AP, Perry GJ. P, Procter DJ. Angew. Chem. Int. Ed. 2019; 58: 15675
37 Kawahara KP, Ito H, Itami K. Chem. Commun. 2023; 59: 1157

38a Ramesh E, Shankar M, Dana S, Sahoo AK. Org. Chem. Front. 2016; 3: 1126
38b Wang X, Gensch T, Glorius F. Org. Chem. Front. 2016; 3: 1619
38c Ramesh E, Guntreddi T, Sahoo AK. Eur. J. Org. Chem. 2017; 4405
38d Saravanan P, Anbarasan P. Org. Lett. 2014; 16: 848
38e Hostier T, Ferey V, Ricci G, Pardo DG, Cossy J. Org. Lett. 2015; 17: 3898

39 Sato R, Onodera A, Goto T, Saito M. Heterocycles 1988; 27: 2563
40 Kawahara KP, Ito H, Itami K. Org. Chem. Front. 2023; 10: 1880
41 Yang S, Cheng R, Zhang M, Bin Z, You J. ACS Catal. 2019; 9: 6188