Citation: Liu Chun, Liu Chao, Li Xin-Min, Gao Zhan-Ming, Jin Zi-Lin. Oxygen-promoted Pd/C-catalyzed Suzuki-Miyaura reaction of potassium aryltrifluoroborates[J]. Chinese Chemical Letters, ;2016, 27(5): 631-634. doi: 10.1016/j.cclet.2015.12.022 shu

Oxygen-promoted Pd/C-catalyzed Suzuki-Miyaura reaction of potassium aryltrifluoroborates

State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116024, China

Corresponding author: Liu Chun, cliu@dlut.edu.cn
Received Date: 19 October 2015
Revised Date: 14 December 2015
Accepted Date: 23 December 2015
Available Online: 6 May 2016

Figures(1)

A simple and highly efficient protocol has been developed for the Pd/C-catalyzed ligand-free Suzuki-Miyaura reaction of potassium aryltrifluoroborates. In this catalytic system, the results demonstrate that oxygen plays a positive role in the cross-coupling reaction. In addition, this catalytic system could be successfully applied to synthesize biaryl compounds containing a carbazolemoiety and the catalyst was recycled seven times without significant loss of catalytic activity.
- Pd/C,
- Oxygen-promoting effect,
- Suzuki-Miyaura reaction,
- Potassium aryltrifluoroborates,
- Carbazole derivatives
1. [1]
  Miyaura N., Suzuki A.. Palladium-catalyzed cross-coupling reactions of organoboron compounds[J]. Chem. Rev., 1995,95:2457-2483.
2. [2]
  Suzuki A.. Recent advances in the cross-coupling reactions of organoboron derivatives with organic electrophiles, 1995-1998[J]. J. Organomet. Chem., 1999,576:147-168.
3. [3]
  Littke A.F., Fu G.C.. Palladium-catalyzed coupling reactions of aryl chlorides[J]. Angew. Chem. Int. Ed., 2002,41:4176-4211.
4. [4]
  Liu C., Zhang Y., Liu N., Qiu J.. A simple and efficient approach for the palladiumcatalyzed ligand-free Suzuki reaction in water[J]. Green Chem., 2012,14:2999-3003.
5. [5]
  D.G. Hall, Structure, Properties, and Preparation of Boronic Acid Derivatives. Overview of Their Reactions and Applications, John Wiley & Sons, Weinheim, Germany, 2005.
6. [6]
  Wong M.S., Zhang X.L.. Ligand promoted palladium-catalyzed homo-coupling of arylboronic acids[J]. Tetrahedron Lett., 2001,42:4087-4089.
7. [7]
  Kuivila H.G., Nahabedian K.V.. Electrophilic displacement reactions. X. General acid catalysis in the protodeboronation of areneboronic acids[J]. J. Am. Chem. Soc, 1961,83:2159-2163.
8. [8]
  Vedejs E., Chapman R.W., Fields S.C., Lin S., Schrimpf M.R.. Conversion of arylboronic acids into potassium aryltrifluoroborates:convenient precursors of arylboron difluoride Lewis acids[J]. J. Org. Chem., 1995,60:3020-3027.
9. [9]
  Darses S., Genet J.P.. Potassium organotrifluoroborates:new perspectives in organic synthesis[J]. Chem. Rev., 2008,108:288-325.
10. [10]
  Molander G.A., Canturk B.. Organotrifluoroborates and monocoordinated palladium complexes as catalysts-A perfect combination for Suzuki-Miyaura coupling[J]. Angew. Chem. Int. Ed., 2009,48:9240-9261.
11. [11]
  Darses S., Genêt J.P., Brayer J.L., Demoute J.P.. Cross-coupling reactions of arenediazonium tetrafluoroborates with potassium aryl-or alkenyltrifluoroborates catalyzed by palladium[J]. Tetrahedron Lett., 1997,38:4393-4396.
12. [12]
  Liu L., Dong Y., Tang N.. A highly efficient and recyclable ligand-free protocol for the Suzuki coupling reaction of potassium aryltrifluoroborates in water[J]. Green Chem., 2014,16:2185-2189.
13. [13]
  Liu L., Dong Y., Pang B., Ma J.. [Bmim] PF₆-promoted ligandless Suzuki-Miyaura coupling reaction of potassium aryltrifluoroborates in water[J]. J. Org. Chem., 2014,79:7193-7198.
14. [14]
  Kitamura Y., Sako S., Udzu T.. Ligand-free Pd/C-catalyzed Suzuki-Miyaura coupling reaction for the synthesis of heterobiaryl derivatives[J]. Chem. Commun, 2007:5069-5071.
15. [15]
  Felpin F.X.. Ten years of adventures with Pd/C catalysts:from reductive processes to coupling reactions[J]. Synlett, 2014,25:1055-1067.
16. [16]
  LeBlond C.R., Butler K.M., Ferrington M.W., Browe M.A.. Palladium on carboncatalyzed cross-coupling of aryl halides with potassium p-tolyltrifluoroborate in air[J]. Synth. Commun., 2009,39:636-640.
17. [17]
  Joucla L., Cusati G., Pinel C., Djakovitch L.. Efficient heterogeneous vinylation of aryl halides using potassium vinyltrifluoroborate[J]. Tetrahedron Lett., 2008,49:4738-4741.
18. [18]
  Joucla L., Cusati G., Pinel C., Djakovitch L.. Heterogeneously Pd/C catalysed procedure for the vinylation of aryl bromides[J]. Appl. Catal., A:Gen., 2009,360:145-153.
19. [19]
  Han W., Liu C., Jin Z.L.. In situ generation of palladium nanoparticles:a simple and highly active protocol for oxygen-promoted ligand-free Suzuki coupling reaction of aryl chlorides[J]. Org. Lett., 2007,9:4005-4007.
20. [20]
  Rao X., Liu C., Xing Y.. Oxygen-promoted palladium-on-carbon-catalyzed ligand-free Suzuki reaction for the synthesis of heterobiaryls in aqueous media[J]. Asian J. Org. Chem., 2013,2:514-518.
21. [21]
  Liu C., Yang W.. A fast and oxygen-promoted protocol for the ligand-free Suzuki reaction of 2-halogenated pyridines in aqueous media[J]. Chem. Commun, 2009:6267-6269.
22. [22]
  Yang W., Liu C., Qiu J.. In situ formation of N,O-bidentate ligand via the hydrogen bond for highly efficient Suzuki reaction of aryl chlorides[J]. Chem. Commun., 2010,46:2659-2661.
23. [23]
  Wang Z.S., Koumura N., Cui Y.. Hexylthiophene-functionalized carbazole dyes for efficient molecular photovoltaics:tuning of solar-cell performance by structural modification[J]. Chem. Mater., 2008,20:3993-4003.
24. [24]
  Barea E.M., Zafer C., Gultekin B.. Quantification of the effects of recombination and injection in the performance of dye-sensitized solar cells based on Nsubstituted carbazole dyes[J]. J. Phys. Chem. C, 2010,114:19840-19848.
25. [25]
  Han W., Liu C., Jin Z.. Aerobic ligand-free Suzuki coupling reaction of aryl chlorides catalyzed by in situ generated palladium nanoparticles at room temperature[J]. Adv. Synth. Catal., 2008,350:501-508.
26. [26]
  Liu C., Ni Q., Bao F., Qiu J.. A simple and efficient protocol for a palladium-catalyzed ligand-free Suzuki reaction at room temperature in aqueous DMF[J]. Green Chem., 2011,13:1260-1266.
27. [27]
  Tsai M.H., Lin H.W., Su H.C.. Highly efficient organic blue electrophosphorescent devices based on 3,6-bis(triphenylsilyl)carbazole as the host material[J]. Adv. Mater., 2006,18:1216-1220.
28. [28]
  Moonsin P., Prachumrak N., Rattanawan R.. Carbazole dendronised triphenylamines as solution processed high T_g amorphous hole-transporting materials for organic electroluminescent devices[J]. Chem. Commun., 2012,48:3382-3384.
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