Synthesis 2023; 55(19): 3159-3171
DOI: 10.1055/a-2107-5307
paper

Suzuki–Miyaura Coupling of Aryl Nosylates with Diethanolamine Boronates

,
Timothé Perrin
,


Abstract

Diethanolamine boronates (DABO boronates) have gained popularity as substrates for Suzuki–Miyaura couplings due to their ease of handling as crystalline, bench-stable solids. Similarly, 4-nitrobenzenesulfonate esters (nosylates), derived from the parent phenols, also possess the advantage of being highly crystalline and stable. Herein, we describe the development of suitable reaction conditions for the Suzuki–Miyaura cross-coupling of DABO boronates with aryl and heteroaryl nosylates.

Supporting Information



Publikationsverlauf

Eingereicht: 06. März 2023

Angenommen nach Revision: 07. Juni 2023

Accepted Manuscript online:
07. Juni 2023

Artikel online veröffentlicht:
04. Juli 2023

© 2023. Thieme. All rights reserved

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  • References

    • 1a Miyaura N, Suzuki A. Chem. Rev. 1995; 95: 2457
    • 1b Chemler SR, Trauner D, Danishefsky SJ. Angew. Chem. Int. Ed. 2001; 40: 4544
    • 1c Metal-Catalyzed Cross-Coupling Reactions . Diederich F, de Meijere A. Wiley-VCH; Weinheim: 2004
    • 1d Brown DG, Boström J. J. Med. Chem. 2016; 59: 4443
    • 1e Magano J, Dunetz JR. Chem. Rev. 2011; 111: 2177
  • 2 For a review, see: Lennox AJ. J, Lloyd-Jones GC. Chem. Soc. Rev. 2014; 43: 412
  • 3 Hall DG. In Structure, Properties, and Preparation of Boronic Acid Derivatives, Vol. 2. Hall DG. Wiley-VCH; Weinheim: 2011
  • 4 Brown HC, Cole TE. Organometallics 1983; 2: 1316
  • 5 Ishiyama T, Murata M, Miyaura N. J. Org. Chem. 1995; 60: 7508
    • 6a Ishiyama T, Takagi J, Ishida K, Miyaura N, Anastasi NR, Hartwig JF. J. Am. Chem. Soc. 2002; 124: 390
    • 6b Mkhalid IA. I, Barnard JH, Marder TB, Murphy JM, Hartwig JF. Chem. Rev. 2010; 110: 890
  • 7 Achilli C, Ciana A, Fagnoni M, Balduini C, Minetti G. Cent. Eur. J. Chem. 2013; 11: 137
    • 9a Mancilla T, Contreras R, Wrackmeyer B. J. Organomet. Chem. 1986; 307: 1
    • 9b Gillis EP, Burke MD. J. Am. Chem. Soc. 2007; 129: 6716
    • 9c Knapp DM, Gillis EP, Burke MD. J. Am. Chem. Soc. 2009; 131: 6961
    • 10a Bonin H, Delbrayelle D, Demonchaux P, Gras E. Chem. Commun. 2010; 46: 2677
    • 10b Reilly MK, Rychnovsky SD. Synlett 2011; 2392
    • 10c Bonin H, Leuma-Yona R, Marchiori B, Demonchaux P, Gras E. Tetrahedron Lett. 2011; 52: 1132
    • 10d Bonin H, Delacroix T, Gras E. Org. Biomol. Chem. 2011; 9: 4714
    • 10e Gigant N, Honraedt A, Gras E, Gillaizeau I. Eur. J. Org. Chem. 2014; 7889
    • 10f Ashworth IW, Campbell AD, Cherryman JH, Clark J, Crampton A, Eden-Rump EG. B, Evans M, Jones MF, McKeever-Abbas S, Meadows RE, Skilling K, Whittaker DT. E, Woodward RL, Inglesby PA. Org. Process Res. Dev. 2018; 22: 1801
    • 10g Inglesby PA, Agnew LR, Carter HL, Ring OT. Org. Process Res. Dev. 2020; 24: 1683
    • 10h Primer DN, Yong K, Ramirez A, Kreilein M, Ferretti AC, Ruda AM, Fleary-Roberts N, Moseley JD, Forsyth SM, Evans GR, Traverse JF. Org. Process Res. Dev. 2022; 26: 1458
  • 12 Prices taken from the Sigma-Aldrich catalogue on 24 Feb 2023. NsCl: USD 64/100 g (USD 142/mol); Tf2O: USD 461/250 g (USD 520/mol); PhNTf2: USD 280/50 g (USD 2001/mol).
    • 13a Cheval NP, Dikova A, Blanc A, Weibel J.-M, Pale P. Chem. Eur. J. 2013; 19: 8765
    • 13b Dikova A, Cheval NP, Blanc A, Weibel J.-M, Pale P. Adv. Synth. Catal. 2015; 357: 4093
    • 13c Dikova A, Cheval NP, Blanc A, Weibel J.-M, Pale P. Tetrahedron 2016; 72: 1960
    • 13d Fang Y, Zhang L, Jin X, Li J, Yuan M, Li R, Wang T, Wang T, Hu H, Gu J. Eur. J. Org. Chem. 2016; 1577
    • 13e Sato Y, Ahida Y, Yoshitake D, Hoshino M, Takemoto T, Tanabe Y. Synthesis 2018; 50: 4659
    • 13f Mohammed S. Orient. J. Chem. 2019; 35: 611
    • 13g Zhao X, Song C, Rainier JD. J. Org. Chem. 2020; 85: 5449

      The triflate analogues of nosylates 1ak have been reported in the literature, with the exception of 1i and 1l:
    • 14a Analogue of 1a: Proutiere F, Schoenebeck F. Angew. Chem. Int. Ed. 2011; 50: 8192
    • 14b Analogue of 1b: Piel I, Steinmetz M, Hirano K, Fröhlich R, Grimme S, Glorius F. Angew. Chem. Int. Ed. 2011; 50: 4983
    • 14c Analogues of 1c and 1k: Huang Z, Liu Z, Zhou J. J. Am. Chem. Soc. 2011; 133: 15882
    • 14d Analogue of 1d: Uchiyama M, Kobayashi Y, Furuyama T, Nakamura S, Kajihara Y, Miyoshi T, Sakamoto T, Kondo Y, Morokuma K. J. Am. Chem. Soc. 2008; 130: 472
    • 14e Analogue of 1e: Edelstein EK, Namirembe S, Morken JP. J. Am. Chem. Soc. 2017; 139: 5027
    • 14f Analogues of 1f, 1g and 1j: Seganish WM, DeShong P. J. Org. Chem. 2004; 69: 1137
    • 14g Analogue of 1h: Vinogradova EV, Park NH, Fors BP, Buchwald SL. Org. Lett. 2013; 15: 1394
  • 15 Chapman EE, Langler RF. J. Sulphur Chem. 2010; 31: 19
  • 16 Pérez-Balado C, Willemsens A, Ormerod D, Aelterman W, Mertens N. Org. Process Res. Dev. 2007; 11: 237
  • 17 Che Z.-P, Yang J.-M, Shan X.-J, Tian Y.-E, Liu S.-M, Lin X.-M, Jiang J, Hu M, Chen G.-Q. J. Asian Nat. Prod. Res. 2020; 22: 678
  • 18 Turcotte V, Fortin S, Vevey F, Coulombe Y, Lacroix J, Côté M.-F, Masson J.-Y, C.-Gaudreault R. J. Med. Chem. 2012; 55: 6194
  • 19 Zhang R, Zhao Y, Liu K.-M, Duan X.-F. Org. Lett. 2018; 20: 7942
  • 20 Liu L, Dong Y, Pang B, Ma J. J. Org. Chem. 2014; 79: 7193
  • 21 So C.-M, Lau C.-P, Kwong F.-Y. Angew. Chem. Int. Ed. 2008; 47: 8059
  • 22 Ferguson J, Zeng F, Alwis N, Alper H. Org. Lett. 2013; 15: 1998
  • 23 Li L, Wang J, Zhou C, Wang R, Hong M. Green Chem. 2011; 13: 2071
  • 24 Li X, Liu Y, Zhang L, Dong Y, Liu Q, Zhang D, Chen L, Zhao Z, Liu H. Green Chem. 2022; 24: 6026
  • 25 Kienle M, Knochel P. Org. Lett. 2010; 12: 2702
  • 26 Diebold C, Becht J.-M, Lu J, Toy P.-H, Le Drian C. Eur. J. Org. Chem. 2012; 893
  • 27 Roth GP, Farina V, Liebeskind LS, Peña-Cabrera E. Tetrahedron Lett. 1995; 36: 2191
  • 28 Debnath B, Gurram RM, Saibal KD, Javed I, Ranjan C, Labanyamoy K. WO2005040102, 2005
  • 29 Ackermann L, Potukuchi HK, Althammer A, Born R, Mayer P. Org. Lett. 2010; 12: 1004
  • 30 Wong PY, Chow WK, Chung KH, So CM, Lau CP, Kwong FY. Chem. Commun. 2011; 47: 8328