Homogeneous Catalyzed Aryl–Aryl Cross-Couplings in Flow

Yosuke Ashikari; Aiichiro Nagaki

doi:10.1055/a-1360-7798

Synthesis, Table of Contents

Synthesis 2021; 53(11): 1879-1888
DOI: 10.1055/a-1360-7798

short review

Homogeneous Catalyzed Aryl–Aryl Cross-Couplings in Flow

Yosuke Ashikari

,

Aiichiro Nagaki∗

Abstract

All articles of this category

Abstract

Aryl–aryl cross-coupling reactions are important reactions for the production of various biaryl compounds. This short review covers the various aryl–aryl cross-coupling reactions carried out in flow, focusing on the metal species of the aryl nucleophiles used in the cross-coupling reactions.

1 Introduction

2 Suzuki–Miyaura Coupling (B)

3 Migita–Kosugi–Stille Coupling (Sn)

4 Negishi Coupling (Zn)

5 Kumada–Tamao–Corriu Coupling (Mg)

6 Murahashi Coupling (Li)

7 Conclusion

Key words

flow microreactors - cross-coupling - reaction integration - aryl metals - flow synthesis

Full Text

References

References

1a Kochi JK, Tamura M. J. Am. Chem. Soc. 1971; 93: 1483
1b Tamao K, Sumitani K, Kumada M. J. Am. Chem. Soc. 1972; 94: 4374
1c Corriu RJ. P, Massse JP. J. Chem. Soc., Chem. Commun. 1972; 144

2a Nicolaou KC, Bulger PG, Sarlah D. Angew. Chem. Int. Ed. 2005; 44: 4442
2b Corbet J.-P, Mignani G. Chem. Rev. 2006; 106: 2651
2c Magano J, Dunetz JR. Chem. Rev. 2011; 111: 2177

3a Miyaura N, Yamada K, Suzuki A. Tetrahedron Lett. 1979; 20: 3437
3b Miyaura N, Suzuki A. J. Chem. Soc., Chem. Commun. 1979; 866
3c Suzuki A. Metal-Catalyzed Cross-Coupling Reactions . Diederich F, Stang PJ. Wiley-VCH; Weinheim: 1998: 49
3d Suzuki A. Handbook of Organopalladium Chemistry for Organic Synthesis. Negishi E. Wiley; New York: 2002: 249

4a Kosugi M, Sasazawa K, Shimizu Y, Migita T. Chem. Lett. 1977; 6: 301
4b Milstein D, Stille JK. J. Am. Chem. Soc. 1978; 100: 3636
4c Stille JK. Angew. Chem., Int. Ed. Engl. 1986; 25: 508

5a King AO, Okukado N, Negishi E. J. Chem. Soc., Chem. Commun. 1977; 683
5b Negishi E. Acc. Chem. Res. 1982; 15: 340

6a Hatanaka Y, Hiyama T. J. Org. Chem. 1988; 53: 918
6b Hiyama T. J. Organomet. Chem. 2002; 653: 58

7 Heravi MM, Zadsirjan V, Hajiabbasi P, Hamidi H. Monatsh. Chem. 2019; 150: 535

8a Murahashi S, Yamamura M, Yanagisawa K, Mita N, Kondo K. J. Org. Chem. 1979; 44: 2408
8b Giannerini M, Fañanás-Mastral M, Feringa BL. Nat. Chem. 2013; 5: 667
8c Firth JD, O’Brien P. ChemCatChem 2015; 7: 395

For books on flow microreactor synthesis, see:

9a Microreactors in Organic Chemistry and Catalysis, 2nd ed. Wirth T. Wiley; New York: 2013
9b Darvas F, Hessel V, Dorman G. Flow Chemistry . DeGruyter; Berlin: 2014
9c Yoshida J. Basics of Flow Microreactor Synthesis . Springer; Tokyo: 2015

For reviews on flow microreactor synthesis, see:

9d Pastre JC, Browne DL, Ley SV. Chem. Soc. Rev. 2013; 42: 8849
9e Baxendale IR. J. Chem. Technol. Biotechnol. 2013; 88: 519
9f Fukuyama T, Totoki T, Ryu I. Green Chem. 2014; 16: 2042
9g Cambié D, Bottecchia C, Straathof NJ. W, Hessel V, Noël T. Chem. Rev. 2016; 116: 10276
9h Kobayashi S. Chem. Asian J. 2016; 11: 425
9i Plutschack MB, Pieber B, Gilmore K, Seeberger PH. Chem. Rev. 2017; 117: 11796
9j Cantillo D, Kappe CO. React. Chem. Eng. 2017; 2: 7
9k Zhao T, Micouin L, Piccardi R. Helv. Chim. Acta 2019; 102: e1900172

Recent examples:

10a Fuse S, Mifune Y, Nakamura H, Tanaka H. Nat. Commun. 2016; 7: 13491
10b Seo H, Katcher MH, Jamison TF. Nat. Chem. 2017; 9: 453
10c Parisi G, Colella M, Monticelli S, Romanazzi G, Holzer W, Langer T, Degennaro L, Pace V, Luisi R. J. Am. Chem. Soc. 2017; 139: 13648
10d Inuki S, Sato K, Fukuyama T, Ryu I, Fujimoto Y. J. Org. Chem. 2017; 82: 1248
10e Islam M, Kariuki BM, Shafiq Z, Wirth T, Ahmed N. Eur. J. Org. Chem. 2019; 1371
10f Miyamura H, Tobita F, Suzuki A, Kobayashi S. Angew. Chem. Int. Ed. 2019; 58: 9220
10g Masui S, Manabe Y, Hirao K, Shimoyama A, Fukuyama T, Ryu I, Fukase K. Synlett 2019; 30: 397
10h Elsherbini M, Winterson B, Alharbi H, Folgueiras-Amador AA, Génot C, Wirth T. Angew. Chem. Int. Ed. 2019; 58: 9811
10i Cambié D, Dobbelaar J, Riente P, Vanderspikken J, Shen C, Seeberger PH, Gilmore K, Debije MG, Noël T. Angew. Chem. Int. Ed. 2019; 58: 14374
10j Ahn G.-N, Yu T, Lee H.-J, Gyak K.-W, Kang J.-H, You D, Kim D.-P. Lab Chip 2019; 19: 3535
10k Ashikari Y, Saito K, Nokami T, Yoshida J, Nagaki A. Chem. Eur. J. 2019; 25: 15239
10l Picard B, Pérez K, Lebleu T, Vuluga D, Burel F, Harrowven DC, Chataigner I, Maddaluno J, Legros J. J. Flow Chem. 2020; 10: 139

11 Lee SL, O’Connor TF, Yang X, Cruz CN, Chatterjee S, Madurawe RD, Moore CM. V, Ya LX, Woodcock J. J. Pharm. Innov. 2015; 10: 191

12a Suga S, Yamada D, Yoshida J. Chem. Lett. 2010; 39: 404
12b Yoshida J, Saito K, Nokami T, Nagaki A. Synlett 2011; 1189

There have already been some marvelous reviews for flow cross-coupling reactions. See:

13a Noël T, Buchwald SL. Chem. Soc. Rev. 2011; 40: 5010
13b Len C, Bruniaux S, Delbecq F, Parmar VS. Catalysts 2017; 7: 146

14a Ishiyama T, Miyaura N. Chem. Rec. 2004; 3: 271
14b Hartwig JF. Chem. Soc. Rev. 2011; 40: 1992
14c Hartwig JF. Acc. Chem. Res. 2012; 45: 864
14d Shimizu M, Hiyama T. Eur. J. Org. Chem. 2013; 8096
14e Shinokubo H. Proc. Jpn. Acad., Ser. B. 2014; 90: 1
14f Browne DL, Baumann M, Harji BH, Baxendale IR, Ley SV. Org. Lett. 2011; 13: 3312

15 Nagaki A, Moriwaki Y, Yoshida J. Chem. Commun. 2012; 48: 11211

16a Flash Chemistry: Fast Organic Synthesis in Microsystems. Yoshida J. John Wiley & Sons; Chichester: 2008

For recent examples, see:

16b Nagaki A, Yamashita H, Hirose K, Tsuchihashi Y, Yoshida J. Angew. Chem. Int. Ed. 2019; 58: 4027
16c Nagaki A, Yamashita H, Hirose K, Tsuchihashi Y, Takumi M, Yoshida J. Chem. Eur. J. 2019; 25: 13719
16d Colella M, Tota A, Takahashi Y, Higuma R, Ishikawa S, Degennaro L, Luisi R, Nagaki A. Angew. Chem. Int. Ed. 2020; 59: 11924
16e Baralle A, Inukai T, Yanagi T, Nogi K, Osuka A, Nagaki A, Yoshida J, Yorimitsu H. Chem. Lett. 2020; 49: 160
16f Ichinari D, Ashikari Y, Mandai K, Aizawa Y, Yoshida J, Nagaki A. Angew. Chem. Int. Ed. 2020; 59: 1567

17a Nagaki A, Kim H, Yoshida J. Angew. Chem. Int. Ed. 2008; 47: 7833
17b Nagaki A, Kim H, Yoshida J. Angew. Chem. Int. Ed. 2009; 48: 8063
17c Nagaki A, Kim H, Usutani H, Matsuo C, Yoshida J. Org. Biomol. Chem. 2010; 8: 1212
17d Nagaki A, Kim H, Moriwaki Y, Matsuo C, Yoshida J. Chem. Eur. J. 2010; 16: 11167
17e Kim H, Nagaki A, Yoshida J. Nat. Commun. 2011; 2: 264
17f Nagaki A. Tetrahedron Lett. 2019; 60: 150923

18 Nagaki A, Takabayashi N, Moriwaki Y, Yoshida J. Chem. Eur. J. 2012; 18: 11871
19 Takahashi Y, Ashikari Y, Takumi M, Shimizu Y, Jiang Y, Higuma R, Ishikawa S, Sakaue H, Shite I, Maekawa K, Aizawa Y, Yamashita H, Yonekura Y, Colella M, Luisi R, Takegawa T, Fujita C, Nagaki A. Eur. J. Org. Chem. 2020; 618
20 Anandan SK, Xiao XY, Patel DV, Ward JS. US Patent 2005197336, 2005
21 Shu S, Pellegatti L, Oberli MA, Buchwald SL. Angew. Chem. Int. Ed. 2011; 50: 10665
22 Giordiano C, Coppi L, Minisci F. US Patent 5312975, 1994
23 Teci M, Tilley M, McGuire MA, Organ MG. Chem. Eur. J. 2016; 22: 17407
24 Noël T, Kuhn S, Musacchio AJ, Jensen KF, Buchwald SL. Angew. Chem. Int. Ed. 2011; 50: 5943

25a Bao Z, Chan WK, Yu L. J. Am. Chem. Soc. 1995; 117: 12426
25b Liang Y, Feng D, Wu Y, Tsai S.-T, Li G, Ray C, Yu L. J. Am. Chem. Soc. 2009; 131: 7792

26 Seyler H, Jones DJ, Holmes AB, Wong WW. H. Chem. Commun. 2012; 48: 1598

27a Coffin RC, Peet J, Rogers J, Bazan GC. Nat. Chem. 2009; 1: 657
27b Nehls BS, Asawapirom U, Füldner S, Preis E, Farrel T, Scherf U. Adv. Funct. Mater. 2004; 14: 352

28 Wang W, Chen R, Hu Y, Lu H, Qiu L, Ding Y, Sun D, Zhang G. J. Mater. Chem. C. 2019; 7: 8450
29 Frischmuth A, Fernández M, Barl NM, Achrainer F, Zipse H, Berionni G, Mayr H, Karaghiosoff K, Knochel P. Angew. Chem. Int. Ed. 2014; 53: 7928
30 Becker MR, Knochel P. Angew. Chem. Int. Ed. 2015; 54: 12501

31a Becker MR, Ganiek MA, Knochel P. Chem. Sci. 2015; 6: 6649
31b Becker MR, Knochel P. Org. Lett. 2016; 18: 1462
31c Ketels M, Ziegler DS, Knochel P. Synlett 2017; 28: 2817

32 Roesner S, Buchwald SL. Angew. Chem. Int. Ed. 2016; 55: 10463

33a Yang Y, Oldenhuis NJ, Buchwald SL. Angew. Chem. Int. Ed. 2013; 52: 615
33b Colombe JR, Bernhardt S, Stathakis C, Buchwald SL, Knochel P. Org. Lett. 2013; 15: 5754

34a Garst JF, Soriaga MP. Coord. Chem. Rev. 2004; 248: 623
34b Seyferth D. Organometallics 2009; 28: 1598

35a Wakami H, Yoshida J. Org. Process Res. Dev. 2005; 9: 787
35b Petersen TP, Becker MR, Knochel P. Angew. Chem. Int. Ed. 2014; 53: 7933
35c Ganiek MA, Becker MR, Ketels M, Knochel P. Org. Lett. 2016; 18: 828
35d Korwar S, Amir S, Tosso PN, Desai BK, Kong CJ, Fadnis S, Telang NS, Ahmad S, Roper TD, Gupton BF. Eur. J. Org. Chem. 2017; 6495

36 Linghu X, Wong N, Jost V, Fantasia S, Sowell CG, Gosselin F. Org. Process Res. Dev. 2017; 21: 1320
37 Linghu X, Wong N, Blake JF, Gaudino JJ, Moffat JG. Complete Accounts of Integrated Drug Discovery and Development: Recent Examples from the Pharmaceutical Industry, Vol. 1. Abdel-Magid AF, Pesti JA, Vaidyanathan R. ACS Symposium Series Vol. 1307; American Chemical Society; Washington DC: 2019. Chap. 1
38 Buono FG, Zhang Y, Tan Z, Brusoe A, Yang B.-S, Lorenz JC, Giovannini R, Song JJ, Yee NK, Senanayake CH. Eur. J. Org. Chem. 2016; 2599

39a Fürstner A, Leitner A. Angew. Chem. Int. Ed. 2002; 41: 609
39b Fürstner A, Martin R. Chem. Lett. 2005; 34: 624
39c Kuzmina OM, Steib AK, Moyeux A, Cahiez G, Knochel P. Synthesis 2015; 47: 1696

40a Fürstner A, Leitner A, Mendez M, Krause H. J. Am. Chem. Soc. 2002; 124: 13856
40b Chua Y.-Y, Duong HA. Chem. Commun. 2014; 50: 8424

41 Wei X.-J, Abdiaj I, Sambiagio C, Li C, Zysman-Colman E, Alcázar J, Noël T. Angew. Chem. Int. Ed. 2019; 58: 13030

42a Nagaki A, Kenmoku A, Moriwaki Y, Hayashi A, Yoshida J. Angew. Chem. Int. Ed. 2010; 49: 7543
42b Nagaki A, Moriwaki Y, Haraki S, Kenmoku A, Hayashi A, Yoshida J. Chem. Asian J. 2012; 7: 1061