Palladium-catalyzed solid-state borylation of aryl halides using mechanochemistry

  1. Koji Kubota1,2ORCID Logo,
  2. Emiru Baba1,
  3. Tamae Seo1,
  4. Tatsuo Ishiyama1 and
  5. Hajime Ito1,2ORCID Logo

1Division of Applied Chemistry, Graduate School of Engineering, Hokkaido University, Sapporo, Hokkaido 060-8628, Japan
2Institute for Chemical Reaction Design and Discovery (WPI-ICReDD), Hokkaido University, Sapporo, Hokkaido 060-8628, Japan

  1. Corresponding author email

This article is part of the thematic issue "Mechanochemistry III".

Guest Editors: J. G. Hernández and L. Borchardt
Beilstein J. Org. Chem. 2022, 18, 855–862. https://doi.org/10.3762/bjoc.18.86
Received 18 Apr 2022, Accepted 09 Jun 2022, Published 18 Jul 2022

  • Letter

Abstract

This study describes the solid-state palladium-catalyzed cross-coupling between aryl halides and bis(pinacolato)diboron using ball milling. The reactions were completed within 10 min for most aryl halides to afford a variety of synthetically useful arylboronates in high yields. Notably, all experimental operations could be performed in air, and did not require the use of large amounts of dry and degassed organic solvents. The utility of this method was further demonstrated by gram-scale synthesis under solvent-free, mechanochemical conditions.

Keywords: ball mill; borylation; cross-coupling; mechanochemistry; solid-state reaction

Introduction

Arylboronic acid and its derivatives are indispensable reagents in modern synthetic chemistry because they have been frequently used for the preparation of many bioactive molecules, natural products, and functional organic materials, typically through Suzuki–Miyaura coupling [1-7]. The palladium-catalyzed boryl substitution of aryl halides with boron reagents, termed Miyaura–Ishiyama borylation, is an efficient method for synthesizing arylboronates with high functional group compatibility [8-14]. To date, many palladium-based catalytic systems in solution for the borylation of aryl halides have been reported [8-14]. However, these solution-based reactions usually require long reaction times and significant amounts of dry and degassed organic solvents. Additionally, to avoid the deterioration of reactivity due to moisture and oxygen, conventional protocols require synthesis techniques that involve the use of high-vacuum Schlenk lines and/or glove boxes, which are costly and require special training to handle. Thus, the development of an operationally simple, solvent-free palladium-catalyzed borylation process applicable for a wide range of aryl halides would greatly improve the practicality of the desired arylboronic acid derivatives.

Nechaev et al. reported the first solvent-free protocol for the palladium-catalyzed Miyaura–Ishiyama borylation of aryl halides in a test tube [15]. They found that a Pd(dba)2/DPEphos catalytic system was effective for aryl bromides, and aryl chlorides reacted more efficiently when XPhos was used as the ligand [15]. Although their achievements are remarkable, this protocol is only applicable to liquid substrates, which can serve as reactants and solvents (neat liquid conditions). In addition, a long reaction time (12 h) is required to complete the reaction [15]. A general and efficient solvent-free borylation protocol that can be applied to liquid as well as solid aryl halides remains undeveloped.

Recently, mechanochemical synthesis using ball milling has attracted considerable attention as an efficient solvent-free synthetic technique [16-33]. Notably, the strong mechanical agitation provided by ball milling enables efficient solid-state organic transformations. Thus far, mechanochemical palladium-catalyzed cross-coupling reactions such as Suzuki–Miyaura [34-47], Buchwald–Hartwig [48-52], Sonogashira [53-56], Negishi [57], Mizoroki–Heck [58-60], and C–S bond-forming [61] reactions have been developed. Our group has also been interested in this class of mechanochemical transformations, particularly in the development of cross-coupling reactions that proceed in the solid state [43-50]. These mechanochemical cross-coupling reactions often show much faster reaction kinetics than those under conventional solution-based conditions because of the high concentration; further, the experimental operations can be carried out in air. Considering these achievements, including our recent success in solid-state cross-coupling chemistry, we envisioned that this mechanochemical strategy could be applied to the palladium-catalyzed borylation of aryl halides [8-14]. The development of a solid-state borylation protocol could provide a practical solution to the many issues associated with conventional solution-based protocols (Scheme 1).

[1860-5397-18-86-i1]

Scheme 1: Development of the first solid-state palladium-catalyzed borylation protocol of aryl halides using mechanochemistry.

Results and Discussion

Initially, we conducted an optimization study on the mechanochemical cross-coupling between 2-bromo-6-methoxynaphthalene (1a, 0.3 mmol) and bis(pinacolato)diboron (2, 1.2 equiv) in the presence of Pd(OAc)2 (2 mol %), KOAc (3.0 equiv), and H2O (60 μL) as a liquid additive [43-45] (Table 1). The reactions were conducted in a Retch MM400 ball mill in a stainless-steel milling jar (1.5 mL) at 30 Hz using one stainless-steel ball (diameter: 5 mm) for 10 min. We used a commercially available temperature-controllable heat gun that was placed directly above the ball-milling jar to control the reaction temperature [45]. Reactions were performed using a heat gun with a preset temperature of 100 °C, and the internal temperature of the reaction mixture (60 °C) was assessed by thermography immediately after opening the milling jar (see Supporting Information File 1 for details). First, we tested various phosphine ligands [62] for this reaction (Table 1, entries 1–8). Interestingly, we found that tri-tert-butylphosphonium tetrafluoroborate (t-Bu3P·HBF4) provided the borylation product 3a in excellent yield (92%, Table 1, entry 1), with a small amount of the protonation product 4a (5%, entry 1). When the reaction was stopped after 5 min, only a 26% yield of 3a was obtained (Table 1, entry 2). The use of 1,1'-bis(diphenylphosphino)ferrocene (dppf), which is the optimal ligand under the original conditions for the solution-based protocol [8], provided only trace amounts of 3a (1%, Table 1, entry 3). Reactions with DPEphos and XPhos, which are the optimal ligands for neat liquid conditions reported by Nechaev [15], also yielded only poor results (Table 1, entries 4 and 5). Other monophosphine ligands, such as SPhos, PCy3, and PAd3, did not improve the yield of 3a (Table 1, entries 6–8). The amount of H2O added was important for the efficiency of the reaction. Decreasing the amount of H2O to 40 μL led to a lower yield of 3a (68%; Table 1, entry 9). The reaction without H2O afforded 3a in only 8% yield (Table 1, entry 10). Finally, we investigated the effect of the reaction temperature. The reaction at a higher temperature (110 °C) also provided 3a in a good yield (90%; Table 1, entry 11), but when the reaction was carried out at 30 °C, the yield was very low (6%; Table 1, entry 12). A longer reaction time (90 min) at 30 °C afforded 3a in a moderate yield (41%; Table 1, entry 13). Note that no homocoupling product of 1a was formed, or only trace amounts (<1%) were formed in all cases.

Table 1: Optimization of the reaction conditions.a

[Graphic 1]
Entry Ligand Amount of H2O (μL) Internal temp (°C) Time (min) Yield of 3a (%)b Yield of 4a (%)b
1 t-Bu3P·HBF4 60 60 10 92 5
2 t-Bu3P·HBF4 60 60 5 26 1
3 dppf 60 60 10 1 <1
4 DPEphos 60 60 10 <1 <1
5 XPhos 60 60 10 5 <1
6 SPhos 60 60 10 2 <1
7 PCy3 60 60 10 5 <1
8 PAd3 60 60 10 6 <1
9 t-Bu3P·HBF4 40 60 10 68 3
10 t-Bu3P·HBF4 0 60 10 8 1
11 t-Bu3P·HBF4 60 110 10 90 6
12 t-Bu3P·HBF4 60 30 10 6 1
13 t-Bu3P·HBF4 60 30 90 41 2

aReaction conditions: a mixture of 1a (0.30 mmol), 2 (0.36 mmol), KOAc (0.9 mmol), Pd(OAc)2 (0.006 mmol), ligand (0.009 mmol), and H2O was milled in a 1.5 mL stainless-steel jar at 30 Hz with one stainless-steel ball that was 5 mm in diameter. bDetermined by GC analysis using an internal standard.

Under the optimized reaction conditions (Table 1, entry 1), we explored the substrate scope of aryl bromides for the solid-state borylation (Scheme 2). The reactions of aryl bromides bearing electron-donating and electron-withdrawing groups at the para position (1b–d) proceeded smoothly to afford the corresponding arylboronates (3b–d) in good to high yields. 4-Bromobiphenyl (1e) also underwent borylation efficiently to form the borylation product (3e) in excellent yield. We found that substrates bearing relatively large conjugated structures (1f−m) tended to show low reactivity under the optimized conditions at 60 °C, but the reactions proceeded smoothly at 110 °C. For example, the bromo-substituted triphenylamine (1f), pyrene (1g and 1h), fluoranthene (1i), biphenyl (1j), triphenylene (1k), tetraphenylethylene (1l), and anthracene (1m) reacted with diboron 2 to form the desired products (3f–m) in high yields.

[1860-5397-18-86-i2]

Scheme 2: Substrate scope of solid aryl bromides. Reaction conditions: a mixture of 1 (0.30 mmol), 2 (0.36 mmol), KOAc (0.9 mmol), Pd(OAc)2 (0.006 mmol), t-Bu3·HBF4 (0.009 mmol), and H2O (60 μL) was milled in a 1.5 mL stainless-steel jar at 30 Hz using one stainless-steel ball that was 5 mm in diameter. The isolated yields are shown. The NMR yields are shown in parentheses.

Next, the substrate scope of liquid aryl bromides was investigated (Scheme 3). We found that the present mechanochemical conditions were applicable to the solid substrate and various liquid substrates (1n–p), and the desired borylation products (3n–p) were obtained in good yields.

[1860-5397-18-86-i3]

Scheme 3: Substrate scope of liquid aryl bromides. Reaction conditions: a mixture of 1 (0.30 mmol), 2 (0.36 mmol), KOAc (0.9 mmol), Pd(OAc)2 (0.006 mmol), t-Bu3·HBF4 (0.009 mmol), and H2O (60 μL) was milled in a 1.5 mL stainless-steel jar at 30 Hz using one stainless-steel ball that was 5 mm in diameter. The isolated yields are shown. The NMR yields are shown in parentheses.

We also investigated the solid-state borylation reactions of aryl iodides and chlorides (Scheme 4). The reaction of 4-iodo-N,N-diphenylaniline (1q) under the optimized conditions at 130 °C for 30 min proceeded smoothly and provided the desired product 3f in high yield (84%). Also, the reaction of (4-chlorophenyl)(phenyl)methanone (1r) afforded the corresponding product 3q in good yield.

[1860-5397-18-86-i4]

Scheme 4: Reactions of solid aryl iodide and chloride. Reaction conditions: a mixture of 1 (0.30 mmol), 2 (0.36 mmol), KOAc (0.9 mmol), Pd(OAc)2 (0.006 mmol), t-Bu3·HBF4 (0.009 mmol), and H2O (60 μL) was milled in a 1.5 mL stainless-steel jar at 30 Hz using one stainless-steel ball that was 5 mm in diameter. The isolated yields are shown. The NMR yields are shown in parentheses.

To demonstrate the practical utility of the developed protocol, the solid-state borylation reaction was investigated on a gram scale (Scheme 5). We carried out the reaction of 1a at 5 mmol in the presence of the optimized catalytic system using a 25 mL stainless-steel jar and four stainless-steel balls (diameter: 10 mm) at 25 Hz and a preset heat-gun temperature of 150 °C. The gram-scale borylation proceeded efficiently and afforded the borylation product 3a in high yield, which was comparable to the yield obtained at the 0.3 mmol scale. We confirmed by thermography that the internal temperature after the reaction was approximately 100 °C.

[1860-5397-18-86-i5]

Scheme 5: Solid-state borylation of aryl halides on a gram scale.

Conclusion

In summary, we have developed the first protocol for the solid-state palladium-catalyzed borylation of aryl halides. This mechanochemical protocol allows the synthesis of various arylboronates in high yields within a short reaction time (within 10 min). Notably, the borylation reactions can be conducted without the use of organic solvents, and all synthetic operations can be carried out in air without the requirement of Schlenk-line techniques or glovebox operations. Therefore, the present solid-state approach is a practical and sustainable method to complement conventional solution-based protocols. The application of this method to the solid-state borylation of insoluble substrates for the synthesis of new arylboronates that are difficult to prepare by other means is currently under investigation.

Supporting Information

Supporting Information File 1: Experimental procedures, experimental set-ups, characterization data, and NMR spectra.
Format: PDF Size: 4.3 MB Download

Acknowledgements

We thank Otsuka Chemical Co., Ltd. for their cooperation and helpful discussion.

Funding

This work was financially supported by the Japan Society for the Promotion of Science (JSPS) via KAKENHI grants 22H00318 and 21H01926; by the JST via CREST grant JPMJCR19R1; FOREST grant JPMJFR201I; and by the Institute for Chemical Reaction Design and Discovery (ICReDD) established by the World Premier International Research Initiative (WPI), MEXT, Japan.

References

  1. Hall, D. G., Ed. Boronic Acids: Preparation and Application in Organic Synthesis, Medicine and Materials, 2nd ed.; Wiley-VCH: Weinheim, Germany, 2011. doi:10.1002/9783527639328
    Return to citation in text: [1]
  2. Diner, C.; Szabó, K. J. J. Am. Chem. Soc. 2017, 139, 2–14. doi:10.1021/jacs.6b10017
    Return to citation in text: [1]
  3. Diaz, D. B.; Yudin, A. K. Nat. Chem. 2017, 9, 731–742. doi:10.1038/nchem.2814
    Return to citation in text: [1]
  4. Touchet, S.; Carreaux, F.; Carboni, B.; Bouillon, A.; Boucher, J.-L. Chem. Soc. Rev. 2011, 40, 3895–3914. doi:10.1039/c0cs00154f
    Return to citation in text: [1]
  5. Smoum, R.; Rubinstein, A.; Dembitsky, V. M.; Srebnik, M. Chem. Rev. 2012, 112, 4156–4220. doi:10.1021/cr608202m
    Return to citation in text: [1]
  6. Mellerup, S. K.; Wang, S. Trends Chem. 2019, 1, 77–89. doi:10.1016/j.trechm.2019.01.003
    Return to citation in text: [1]
  7. Budiman, Y. P.; Westcott, S. A.; Radius, U.; Marder, T. B. Adv. Synth. Catal. 2021, 363, 2224–2255. doi:10.1002/adsc.202001291
    Return to citation in text: [1]
  8. Ishiyama, T.; Murata, M.; Miyaura, N. J. Org. Chem. 1995, 60, 7508–7510. doi:10.1021/jo00128a024
    Return to citation in text: [1] [2] [3] [4]
  9. Ishiyama, T.; Itoh, Y.; Kitano, T.; Miyaura, N. Tetrahedron Lett. 1997, 38, 3447–3450. doi:10.1016/s0040-4039(97)00642-4
    Return to citation in text: [1] [2] [3]
  10. Ishiyama, T.; Ishida, K.; Miyaura, N. Tetrahedron 2001, 57, 9813–9816. doi:10.1016/s0040-4020(01)00998-x
    Return to citation in text: [1] [2] [3]
  11. Chow, W. K.; Yuen, O. Y.; Choy, P. Y.; So, C. M.; Lau, C. P.; Wong, W. T.; Kwong, F. Y. RSC Adv. 2013, 3, 12518–12539. doi:10.1039/c3ra22905j
    Return to citation in text: [1] [2] [3]
  12. Barroso, S.; Joksch, M.; Puylaert, P.; Tin, S.; Bell, S. J.; Donnellan, L.; Duguid, S.; Muir, C.; Zhao, P.; Farina, V.; Tran, D. N.; de Vries, J. G. J. Org. Chem. 2021, 86, 103–109. doi:10.1021/acs.joc.0c01758
    Return to citation in text: [1] [2] [3]
  13. Murata, M.; Oyama, T.; Watanabe, S.; Masuda, Y. J. Org. Chem. 2000, 65, 164–168. doi:10.1021/jo991337q
    Return to citation in text: [1] [2] [3]
  14. Kubota, K.; Iwamoto, H.; Ito, H. Org. Biomol. Chem. 2017, 15, 285–300. doi:10.1039/c6ob02369j
    Return to citation in text: [1] [2] [3]
  15. Dzhevakov, P. B.; Topchiy, M. A.; Zharkova, D. A.; Morozov, O. S.; Asachenko, A. F.; Nechaev, M. S. Adv. Synth. Catal. 2016, 358, 977–983. doi:10.1002/adsc.201500844
    Return to citation in text: [1] [2] [3] [4]
  16. James, S. L.; Adams, C. J.; Bolm, C.; Braga, D.; Collier, P.; Friščić, T.; Grepioni, F.; Harris, K. D. M.; Hyett, G.; Jones, W.; Krebs, A.; Mack, J.; Maini, L.; Orpen, A. G.; Parkin, I. P.; Shearouse, W. C.; Steed, J. W.; Waddell, D. C. Chem. Soc. Rev. 2012, 41, 413–447. doi:10.1039/c1cs15171a
    Return to citation in text: [1]
  17. Bowmaker, G. A. Chem. Commun. 2013, 49, 334–348. doi:10.1039/c2cc35694e
    Return to citation in text: [1]
  18. Wang, G.-W. Chem. Soc. Rev. 2013, 42, 7668–7700. doi:10.1039/c3cs35526h
    Return to citation in text: [1]
  19. Hernández, J. G.; Bolm, C. J. Org. Chem. 2017, 82, 4007–4019. doi:10.1021/acs.joc.6b02887
    Return to citation in text: [1]
  20. Stolle, A.; Szuppa, T.; Leonhardt, S. E. S.; Ondruschka, B. Chem. Soc. Rev. 2011, 40, 2317–2329. doi:10.1039/c0cs00195c
    Return to citation in text: [1]
  21. Kubota, K.; Ito, H. Trends Chem. 2020, 2, 1066–1081. doi:10.1016/j.trechm.2020.09.006
    Return to citation in text: [1]
  22. Howard, J. L.; Cao, Q.; Browne, D. L. Chem. Sci. 2018, 9, 3080–3094. doi:10.1039/c7sc05371a
    Return to citation in text: [1]
  23. Braga, D.; Maini, L.; Grepioni, F. Chem. Soc. Rev. 2013, 42, 7638–7648. doi:10.1039/c3cs60014a
    Return to citation in text: [1]
  24. Achar, T. K.; Bose, A.; Mal, P. Beilstein J. Org. Chem. 2017, 13, 1907–1931. doi:10.3762/bjoc.13.186
    Return to citation in text: [1]
  25. Do, J.-L.; Friščić, T. ACS Cent. Sci. 2017, 3, 13–19. doi:10.1021/acscentsci.6b00277
    Return to citation in text: [1]
  26. Métro, T.-X.; Martinez, J.; Lamaty, F. ACS Sustainable Chem. Eng. 2017, 5, 9599–9602. doi:10.1021/acssuschemeng.7b03260
    Return to citation in text: [1]
  27. Eguaogie, O.; Vyle, J. S.; Conlon, P. F.; Gîlea, M. A.; Liang, Y. Beilstein J. Org. Chem. 2018, 14, 955–970. doi:10.3762/bjoc.14.81
    Return to citation in text: [1]
  28. Bolm, C.; Hernández, J. G. Angew. Chem., Int. Ed. 2019, 58, 3285–3299. doi:10.1002/anie.201810902
    Return to citation in text: [1]
  29. Friščić, T.; Mottillo, C.; Titi, H. M. Angew. Chem., Int. Ed. 2020, 59, 1018–1029. doi:10.1002/anie.201906755
    Return to citation in text: [1]
  30. Andersen, J.; Mack, J. Green Chem. 2018, 20, 1435–1443. doi:10.1039/c7gc03797j
    Return to citation in text: [1]
  31. Porcheddu, A.; Colacino, E.; De Luca, L.; Delogu, F. ACS Catal. 2020, 10, 8344–8394. doi:10.1021/acscatal.0c00142
    Return to citation in text: [1]
  32. Leitch, J. A.; Browne, D. L. Chem. – Eur. J. 2021, 27, 9721–9726. doi:10.1002/chem.202100348
    Return to citation in text: [1]
  33. Kaupp, G. CrystEngComm 2009, 11, 388–403. doi:10.1039/b810822f
    Return to citation in text: [1]
  34. Schneider, F.; Ondruschka, B. ChemSusChem 2008, 1, 622–625. doi:10.1002/cssc.200800086
    Return to citation in text: [1]
  35. Cravotto, G.; Garella, D.; Tagliapietra, S.; Stolle, A.; Schüßler, S.; Leonhardt, S. E. S.; Ondruschka, B. New J. Chem. 2012, 36, 1304–1307. doi:10.1039/c2nj40064b
    Return to citation in text: [1]
  36. Nielsen, S. F.; Peters, D.; Axelsson, O. Synth. Commun. 2000, 30, 3501–3509. doi:10.1080/00397910008087262
    Return to citation in text: [1]
  37. Klingensmith, L. M.; Leadbeater, N. E. Tetrahedron Lett. 2003, 44, 765–768. doi:10.1016/s0040-4039(02)02645-x
    Return to citation in text: [1]
  38. Bernhardt, F.; Trotzki, R.; Szuppa, T.; Stolle, A.; Ondruschka, B. Beilstein J. Org. Chem. 2010, 6, No. 7. doi:10.3762/bjoc.6.7
    Return to citation in text: [1]
  39. Schneider, F.; Szuppa, T.; Stolle, A.; Ondruschka, B.; Hopf, H. Green Chem. 2009, 11, 1894–1899. doi:10.1039/b915744c
    Return to citation in text: [1]
  40. Schneider, F.; Stolle, A.; Ondruschka, B.; Hopf, H. Org. Process Res. Dev. 2009, 13, 44–48. doi:10.1021/op800148y
    Return to citation in text: [1]
  41. Jiang, Z.-J.; Li, Z.-H.; Yu, J.-B.; Su, W.-K. J. Org. Chem. 2016, 81, 10049–10055. doi:10.1021/acs.joc.6b01938
    Return to citation in text: [1]
  42. Báti, G.; Csókás, D.; Yong, T.; Tam, S. M.; Shi, R. R. S.; Webster, R. D.; Pápai, I.; García, F.; Stuparu, M. C. Angew. Chem., Int. Ed. 2020, 59, 21620–21626. doi:10.1002/anie.202007815
    Return to citation in text: [1]
  43. Seo, T.; Ishiyama, T.; Kubota, K.; Ito, H. Chem. Sci. 2019, 10, 8202–8210. doi:10.1039/c9sc02185j
    Return to citation in text: [1] [2] [3]
  44. Seo, T.; Kubota, K.; Ito, H. J. Am. Chem. Soc. 2020, 142, 9884–9889. doi:10.1021/jacs.0c01739
    Return to citation in text: [1] [2] [3]
  45. Seo, T.; Toyoshima, N.; Kubota, K.; Ito, H. J. Am. Chem. Soc. 2021, 143, 6165–6175. doi:10.1021/jacs.1c00906
    Return to citation in text: [1] [2] [3] [4]
  46. Takahashi, R.; Seo, T.; Kubota, K.; Ito, H. ACS Catal. 2021, 11, 14803–14810. doi:10.1021/acscatal.1c03731
    Return to citation in text: [1] [2]
  47. Kubota, K.; Kondo, K.; Seo, T.; Ito, H. Synlett 2022, 33, 898–902. doi:10.1055/a-1748-3797
    Return to citation in text: [1] [2]
  48. Kubota, K.; Seo, T.; Koide, K.; Hasegawa, Y.; Ito, H. Nat. Commun. 2019, 10, No. 111. doi:10.1038/s41467-018-08017-9
    Return to citation in text: [1] [2]
  49. Kubota, K.; Takahashi, R.; Uesugi, M.; Ito, H. ACS Sustainable Chem. Eng. 2020, 8, 16577–16582. doi:10.1021/acssuschemeng.0c05834
    Return to citation in text: [1] [2]
  50. Kubota, K.; Endo, T.; Uesugi, M.; Hayashi, Y.; Ito, H. ChemSusChem 2022, 15, e202102132. doi:10.1002/cssc.202102132
    Return to citation in text: [1] [2]
  51. Shao, Q.-L.; Jiang, Z.-J.; Su, W.-K. Tetrahedron Lett. 2018, 59, 2277–2280. doi:10.1016/j.tetlet.2018.04.078
    Return to citation in text: [1]
  52. Cao, Q.; Nicholson, W. I.; Jones, A. C.; Browne, D. L. Org. Biomol. Chem. 2019, 17, 1722–1726. doi:10.1039/c8ob01781f
    Return to citation in text: [1]
  53. Fulmer, D. A.; Shearouse, W. C.; Medonza, S. T.; Mack, J. Green Chem. 2009, 11, 1821–1825. doi:10.1039/b915669k
    Return to citation in text: [1]
  54. Liang, Y.; Xie, Y.-X.; Li, J.-H. J. Org. Chem. 2006, 71, 379–381. doi:10.1021/jo051882t
    Return to citation in text: [1]
  55. Thorwirth, R.; Stolle, A.; Ondruschka, B. Green Chem. 2010, 12, 985–991. doi:10.1039/c000674b
    Return to citation in text: [1]
  56. Gao, Y.; Feng, C.; Seo, T.; Kubota, K.; Ito, H. Chem. Sci. 2022, 13, 430–438. doi:10.1039/d1sc05257h
    Return to citation in text: [1]
  57. Cao, Q.; Howard, J. L.; Wheatley, E.; Browne, D. L. Angew. Chem., Int. Ed. 2018, 57, 11339–11343. doi:10.1002/anie.201806480
    Return to citation in text: [1]
  58. Declerck, V.; Colacino, E.; Bantreil, X.; Martinez, J.; Lamaty, F. Chem. Commun. 2012, 48, 11778–11780. doi:10.1039/c2cc36286d
    Return to citation in text: [1]
  59. Tullberg, E.; Schacher, F.; Peters, D.; Frejd, T. Synthesis 2006, 1183–1189. doi:10.1055/s-2006-926371
    Return to citation in text: [1]
  60. Tullberg, E.; Peters, D.; Frejd, T. J. Organomet. Chem. 2004, 689, 3778–3781. doi:10.1016/j.jorganchem.2004.06.045
    Return to citation in text: [1]
  61. Jones, A. C.; Nicholson, W. I.; Smallman, H. R.; Browne, D. L. Org. Lett. 2020, 22, 7433–7438. doi:10.1021/acs.orglett.0c02418
    Return to citation in text: [1]
  62. Tang, W.; Keshipeddy, S.; Zhang, Y.; Wei, X.; Savoie, J.; Patel, N. D.; Yee, N. K.; Senanayake, C. H. Org. Lett. 2011, 13, 1366–1369. doi:10.1021/ol2000556
    Return to citation in text: [1]

Article is part of the thematic issue

Mechanochemistry III

José G. Hernández and Lars Borchardt

Interesting articles

DDQ in mechanochemical C–N coupling reactions

Shyamal Kanti Bera, Rosalin Bhanja and Prasenjit Mal

Multi-faceted reactivity of N-fluorobenzenesulfonimide (NFSI) under mechanochemical conditions: fluorination, fluorodemethylation, sulfonylation, and amidation reactions

José G. Hernández, Karen J. Ardila-Fierro, Dajana Barišić and Hervé Geneste

Mechanochemical synthesis of poly(trimethylene carbonate)s: an example of rate acceleration

Sora Park and Jeung Gon Kim

News

Online Beilstein Talk with Jeroen S. Dickschat May 4 – Register for free!
Logo OA

Beilstein Glyco-Bioinformatics Symposium 2023 - June 20 to 22, 2023, Limburg, Germany
Logo OA

Take a look at the research you were most interested in last year
Logo OA

© 2022 Kubota et al.; licensee Beilstein-Institut.
This is an open access article licensed under the terms of the Beilstein-Institut Open Access License Agreement (https://www.beilstein-journals.org/bjoc/terms), which is identical to the Creative Commons Attribution 4.0 International License (https://creativecommons.org/licenses/by/4.0). The reuse of material under this license requires that the author(s), source and license are credited. Third-party material in this article could be subject to other licenses (typically indicated in the credit line), and in this case, users are required to obtain permission from the license holder to reuse the material.

 
Back to Article List

Other Beilstein-Institut Open Science Activities

Logo
Logo
Logo
Logo

Keep Informed

RSS Feed

Subscribe to our Latest Articles RSS Feed.

Subscribe

Follow the Beilstein-Institut

LinkedIn

Twitter: @BeilsteinInst