Insight into the Reactivity Profile of Solid-State Aryl Bromides in Suzuki–Miyaura Cross-Coupling Reactions Using Ball Milling

Abstract

Despite recent advances in solid-state organic synthesis using ball milling, insight into the unique reactivity of solid-state substrates, which is often different from that in solution, has been poorly explored. In this study, we investigated the relationship between the reactivity and melting points of aryl halides in solid-state Suzuki–Miyaura cross-coupling reactions and the effect of reaction temperature on these processes. We found that aryl halides with high melting points showed significantly low reactivity in the solid-state cross-coupling near room temperature, but the reactions were notably accelerated by increasing the reaction temperature. Given that the reaction temperature is much lower than the melting points of these substrates, the acceleration effect is most likely ascribed to the weakening of the intermolecular interactions between the substrate molecules in the solid state. The present study provides important perspectives for the rational design of efficient solid-state organic transformations using ball milling.

Key words

cross-coupling - solid state - mechanochemistry - ball milling - palladium catalyst

Publication History

Received: 09 December 2021

Accepted after revision: 21 January 2022

Accepted Manuscript online:
21 January 2022

Article published online:
04 March 2022

• References and Notes


For selected reviews on reaction development using mechanochemistry, see:
• 1a James SL, Adams CJ, Bolm C, Braga D, Collier P, Friščić T, Grepioni F, Harris KD. M, Hyett G, Jones W, Krebs A, Mack J, Maini L, Orpen AG, Parkin IP, Shearouse WC, Steed JW, Waddell DC. Chem. Soc. Rev. 2012; 41: 413
• 1b Wang G.-W. Chem. Soc. Rev. 2013; 42: 7668
• 1c Do J.-L, Friščić T. ACS Cent. Sci. 2017; 3: 13
• 1d Hernández JG, Bolm C. J. Org. Chem. 2017; 82: 4007
• 1e Métro T.-X, Martinez J, Lamaty F. ACS Sustainable Chem. Eng. 2017; 5: 9599
• 1f Achar TK, Bose A, Mal P. Beilstein J. Org. Chem. 2017; 13: 1907
• 1g Eguaogie O, Vyle JS, Conlon PF, Gîlea MA, Liang Y. Beilstein J. Org. Chem. 2018; 14: 955
• 1h Howard JL, Cao Q, Browne DL. Chem. Sci. 2018; 9: 3080
• 1i Andersen J, Mack J. Green Chem. 2018; 20: 1435
• 1j Bolm C, Hernández JG. Angew. Chem. Int. Ed. 2019; 58: 3285
• 1k Friščić T, Mottillo C, Titi HM. Angew. Chem. Int. Ed. 2020; 59: 1018
• 1l Kubota K, Ito H. Trends Chem. 2020; 2: 1066
• 1m Porcheddu A, Colacino E, De Luca L, Delogu F. ACS Catal. 2020; 10: 8344
• 1n Leitch JA, Browne DL. Chem. Eur. J. 2021; 27: 9721
• 1o Kaupp G. CrystEngComm 2009; 11: 388

For selected examples of solid-state organic transformations using ball milling from our group, see:
• 2a Kubota K, Pang Y, Miura A, Ito H. Science 2019; 366: 1500
• 2b Pang Y, Ishiyama T, Kubota K, Ito H. Chem. Eur. J. 2019; 25: 4654
• 2c Kubota K, Takahashi R, Ito H. Chem. Sci. 2019; 10: 5837
• 2d Kubota K, Seo T, Koide K, Hasegawa S, Ito H. Nat. Commun. 2019; 10: 111
• 2e Pang Y, Lee JW, Kubota K, Ito H. Angew. Chem. Int. Ed. 2020; 59: 22570
• 2f Kubota K, Toyoshima N, Miura D, Jiang J, Maeda S, Jin M, Ito H. Angew. Chem. Int. Ed. 2021; 60: 16003
• 2g Takahashi R, Hu A, Gao P, Gao Y, Pang Y, Seo T, Maeda S, Jiang J, Takaya H, Kubota K, Ito H. Nat. Commun. 2021; 12: 6691
• 3a Tanaka K. Solvent-Free Organic Synthesis, 2nd ed. . Wiley-VCH; Weinheim: 2009
• 3b Toda F. Organic Solid-State Reactions. Springer; Berlin/Heidelberg: 2004
• 3c Toda F. Acc. Chem. Res. 1995; 28: 480
• 3d Tanaka K, Toda F. Chem. Rev. 2000; 100: 1025
• 3e Kaupp G. Top. Curr. Chem. 2005; 254: 95
• 4 Zhao Y, Rocha SV, Swager TM. J. Am. Chem. Soc. 2016; 138: 13834
• 5 Seo T, Kubota K, Ito H. J. Am. Chem. Soc. 2020; 142: 9884
• 6 Do J.-L, Mottillo C, Tan D, Štrukil V, Friščić T. J. Am. Chem. Soc. 2015; 137: 2476
• 7 Komatsu K, Wang G.-W, Murata Y, Shiro M. Nature 1997; 387: 583
• 8 Takahashi R, Seo T, Kubota K, Ito H. ACS Catal. 2021; 11: 14803
• 9 Howard JL, Brand MC, Browne DL. Angew. Chem. Int. Ed. 2018; 57: 16104
• 10 Belenguer AM, Frisić T, Day GM, Sanders JK. M. Chem. Sci. 2011; 2: 696
• 11 Shi YX, Xu K, Clegg JK, Ganguly R, Hirao H, Friščić T, García F. Angew. Chem. Int. Ed. 2016; 55: 12736
• 12 Seo T, Ishiyama T, Kubota K, Ito H. Chem. Sci. 2019; 10: 8202
• 13a Schneider F, Ondruschka B. ChemSusChem 2008; 1: 622
• 13b Schneider F, Szuppa T, Stolle A, Ondruschka B, Hopf H. Green Chem. 2009; 11: 1894
• 14 Seo T, Toyoshima N, Kubota K, Ito H. J. Am. Chem. Soc. 2021; 143: 6165
• 15 Báti G, Csókás D, Yong T, Tam SM, Shi RR. S, Webster RD, Pápai I, Garcia F, Stuparu MC. Angew. Chem. Int. Ed. 2020; 59: 21620

The selected review on palladium-catalyzed cross-coupling chemistry, see:
• 16a Johansson Seehurn CC. C, Kitching MO, Colacot TJ, Snieckus V. Angew. Chem. Int. Ed. 2012; 51: 5062
• 16b Molnár A. Palladium-Catalyzed Coupling Reactions: Practical Aspects and Future Developments. Wiley-VCH; Weinheim: 2013
• 16c Meijere A, Diederich F. Metal-Catalyzed Cross-Coupling Reactions, 2nd ed. Wiley-VCH; Weinheim: 2008
• 16d Miyaura N, Suzuki A. Chem. Rev. 1995; 95: 2457
• 16e Lennox AJ. J, Lloyd-Jones GC. Chem. Soc. Rev. 2014; 43: 412
• 16f Martin R, Buchwald SL. Acc. Chem. Res. 2008; 41: 1461
• 16g Ruiz-Castillo P, Buchwald SL. Chem. Rev. 2016; 116: 12564
• 16h Sather AC, Buchwald SL. Acc. Chem. Res. 2016; 49: 2146
• 16i Roy D, Uozumi Y. Adv. Synth. Catal. 2018; 360: 602
• 16j Ingoglia BT, Wagen CC, Buchwald SL. Tetrahedron 2019; 75: 4199