Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Pd/C-Catalyzed Oxidative Alkylation of Secondary Alcohols with Primary Alcohols

  • Cho, Chan-Sik (Research Institute of Industrial Technology, Kyungpook National University) ;
  • Ren, Wen Xiu (Department of Applied Chemistry, College of Engineering, Kyungpook National University) ;
  • Shim, Sang-Chul (Department of Applied Chemistry, College of Engineering, Kyungpook National University)
  • Published : 2005.10.20
Download PDF
⟨ Previous Next ⟩

Abstract

Keywords

References

  1. Metal-catalyzed Cross-coupling Reactions; Stang, P. J., Diederich, F., Eds.; Wiley-VCH: Weinheim, 1998
  2. Cho, C. S.; Kim, B. T.; Kim, T.-J.; Shim, S. C. Tetrahedron Lett. 2002, 43, 7987 https://doi.org/10.1016/S0040-4039(02)01625-8
  3. Cho, C. S.; Kim, B. T.; Kim, T.-J.; Shim, S. C. J. Org. Chem. 2001, 66, 9022
  4. Cho, C. S.; Kim, B. T.; Kim, H.-S.; Kim, T.-J.; Shim, S. C. Organometallics 2003, 22, 3608 https://doi.org/10.1021/om030307h
  5. Cho, C. S.; Kim, B. T.; Lee, M. J.; Kim, T.-J.; Shim, S. C. Angew. Chem., Int. Ed. 2001, 40, 958 https://doi.org/10.1002/1521-3773(20010302)40:5<958::AID-ANIE958>3.0.CO;2-4
  6. Cho, C. S. J. Mol. Cat. A: Chem. 2005, 240, 55
  7. Taguchi, K.; Nakagawa, H.; Hirabayashi, T.; Sakaguchi, S.; Ishii, Y. J. Am. Chem. Soc. 2004, 126, 72 https://doi.org/10.1021/ja037552c
  8. Cho, C. S.; Kim, B. T.; Kim, T.-J.; Shim, S. C. Chem. Commun. 2001, 2576
  9. Cho, C. S.; Kim, B. T.; Choi, H.-J.; Kim, T.-J.; Shim, S. C. Tetrahedron 2003, 59, 7997 https://doi.org/10.1016/j.tet.2003.08.027
  10. Motokura, K.; Mizugaki, T.; Ebitani, K.; Kaneda, K. Tetrahedron Lett. 2004, 45, 6029 https://doi.org/10.1016/j.tetlet.2004.06.023
  11. Taguchi, K.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 2005, 46, 4539 https://doi.org/10.1016/j.tetlet.2005.05.013
  12. Cho, C. S.; Lim, D. K.; Heo, N. H.; Kim, T.-J.; Shim, S. C. Chem. Commun. 2004, 104
  13. Cho, C. S.; Lim, D. K.; Zhang, J. Q.; Kim, T.-J.; Shim, S. C. Tetrahedron Lett. 2004, 45, 5653 https://doi.org/10.1016/j.tetlet.2004.05.112
  14. Zassinovich, G.; Mestroni, G.; Gladiali, S. Chem. Rev. 1992, 92, 1051 https://doi.org/10.1021/cr00013a015
  15. Backvall, J.-E.; Chowdhury, R. L.; Karlsson, U.; Wang, G. Perspectives in Coordination Chemistry; Williams, A. F.; Floriani, C.; Merbach, A. E. Eds.; VCH: New York, 1992; pp 463-486
  16. Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 97 https://doi.org/10.1021/ar9502341
  17. Naota, T.; Takaya, H.; Murahashi, S.- I. Chem. Rev. 1998, 98, 2599 https://doi.org/10.1021/cr9403695
  18. Palmer, M.; Wills, M. Tetrahedron: Asymmetry 1999, 10, 2045 https://doi.org/10.1016/S0957-4166(99)00216-5
  19. Shen, H.-C.; Su, H.-L.; Hsueh, Y.-C.; Liu, R.-S. Organometallics 2004, 23, 4332 https://doi.org/10.1021/om049711m
  20. Whitmore, F. C.; Schiessler, R. W.; Rowland, C. S.; Cosby, J. N. J. Am. Chem. Soc. 1947, 69, 235 https://doi.org/10.1021/ja01194a016
  21. Rothstein, E.; Schofield, W. G. J. Chem. Soc. 1965, 4566 https://doi.org/10.1039/jr9650004566
  22. Shimada, T.; Yamamoto, Y. J. Am. Chem. Soc. 2002, 124, 12670 https://doi.org/10.1021/ja027683y
  23. Kaneko, Y.; Sarker, A. M.; Neckers, D. C. Chem. Mater. 1999, 11, 170 https://doi.org/10.1021/cm980618w

Cited by

  1. Dehydrogenative Cross-Coupling of Primary and Secondary Alcohols vol.355, pp.14-15, 2013, https://doi.org/10.1002/adsc.201300656
  2. Alkylation of Methyl Carbinols with Alcohols vol.355, pp.4, 2013, https://doi.org/10.1002/adsc.201200996
  3. Tris(acetylacetonato)rhodium(III)-Catalyzed α-Alkylation of Ketones, β-Alkylation of Secondary Alcohols and Alkylation of Amines with Primary Alcohols vol.355, pp.9, 2013, https://doi.org/10.1002/adsc.201300061
  4. CC Cross-Coupling of Primary and Secondary Benzylic Alcohols Using Supported Gold-Based Bimetallic Catalysts vol.6, pp.4, 2013, https://doi.org/10.1002/cssc.201200804
  5. Ruthenium-Catalyzed Self-Coupling of Primary and Secondary Alcohols with the Liberation of Dihydrogen vol.78, pp.13, 2013, https://doi.org/10.1021/jo4008699
  6. Efficient photocatalytic Suzuki cross-coupling reactions on Au–Pd alloy nanoparticles under visible light irradiation vol.16, pp.9, 2014, https://doi.org/10.1039/C4GC00588K
  7. Alkylation Reactions using Alcohols with Hydrogen Borrowing Methodologies vol.4, pp.11, 2014, https://doi.org/10.1021/cs501269d
  8. Self-Coupling of Secondary Alcohols and α-Alkylation of Methyl Ketones with Secondary Alcohols by Pt/CeO2 Catalyst vol.57, pp.10-13, 2014, https://doi.org/10.1007/s11244-014-0268-6
  9. Co–N–C Catalyst for C–C Coupling Reactions: On the Catalytic Performance and Active Sites vol.5, pp.11, 2015, https://doi.org/10.1021/acscatal.5b01223
  10. Heterogeneous catalysis for the direct synthesis of chemicals by borrowing hydrogen methodology vol.5, pp.3, 2015, https://doi.org/10.1039/C4CY01170H
  11. Cu–Ag/hydrotalcite catalysts for dehydrogenative cross-coupling of primary and secondary benzylic alcohols vol.6, pp.29, 2016, https://doi.org/10.1039/C5RA22542F
  12. Efficient and versatile catalysis for β-alkylation of secondary alcohols through hydrogen auto transfer process with newly designed ruthenium(II) complexes containing ON donor aldazine ligands vol.70, pp.17, 2017, https://doi.org/10.1080/00958972.2017.1381692
  13. C-C-Kupplungen mit Alkoholen als Elektrophilen: der Wasserstoff-Autotransfer vol.119, pp.14, 2007, https://doi.org/10.1002/ange.200603794
  14. Alcohols as Electrophiles in CC Bond-Forming Reactions: The Hydrogen Autotransfer Process vol.46, pp.14, 2007, https://doi.org/10.1002/anie.200603794
  15. CH Activation Catalyzed by a Ruthenium/Lewis Acid System vol.14, pp.33, 2008, https://doi.org/10.1002/chem.200801317
  16. Direct CC Cross-Coupling of Secondary and Primary Alcohols Catalyzed by a γ-Alumina-Supported Silver Subnanocluster vol.48, pp.22, 2009, https://doi.org/10.1002/anie.200901057
  17. Direct CC Cross-Coupling of Secondary and Primary Alcohols Catalyzed by a γ-Alumina-Supported Silver Subnanocluster vol.121, pp.22, 2009, https://doi.org/10.1002/ange.200901057
  18. Pd/C-Catalyzed Oxidative Alkylation of Secondary Alcohols with Primary Alcohols. vol.37, pp.10, 2005, https://doi.org/10.1002/chin.200610068
  19. Catalytic C−C Coupling via Transfer Hydrogenation: Reverse Prenylation, Crotylation, and Allylation from the Alcohol or Aldehyde Oxidation Level vol.129, pp.49, 2007, https://doi.org/10.1021/ja077389b
  20. Pd‐Catalyzed Hydrogen‐Transfer Reactions from Alcohols to C=C, C=O, and C=N Bonds vol.2015, pp.26, 2005, https://doi.org/10.1002/ejoc.201500401
  21. Hydrogen auto-transfer under aerobic oxidative conditions: Efficient synthesis of saturated ketones by aerobic C-C cross-coupling of primary and secondary alcohols catalyzed by a Au6Pd/resin catalyst vol.37, pp.10, 2005, https://doi.org/10.1016/s1872-2067(16)62511-1
  22. C-Alkylation by Hydrogen Autotransfer Reactions vol.374, pp.2, 2005, https://doi.org/10.1007/s41061-016-0012-8
  23. Ruthenium Phosphine–Pyridone Catalyzed Cross-Coupling of Alcohols To form α-Alkylated Ketones vol.82, pp.19, 2005, https://doi.org/10.1021/acs.joc.7b02042
  24. Ligand-Controlled Copper(I)-Catalyzed Cross-Coupling of Secondary and Primary Alcohols to α-Alkylated Ketones, Pyridines, and Quinolines vol.20, pp.3, 2005, https://doi.org/10.1021/acs.orglett.7b03726
  25. Iridium(I)-Catalyzed Alkylation Reactions To Form α-Alkylated Ketones vol.83, pp.5, 2005, https://doi.org/10.1021/acs.joc.8b00043