Crossref journal-article
Wiley
Advanced Synthesis & Catalysis (311)
Abstract

AbstractAcylation of secondary alcohols using non‐activated esters, in particular symmetrical esters (such as ethyl acetate), is achieved under neutral conditions with the liberation of molecular hydrogen. This unprecedented, environmentally benign reaction is homogenously catalyzed by a dearomatized ruthenium pincer PNN complex.

Bibliography

Gnanaprakasam, B., Ben‐David, Y., & Milstein, D. (2010). Ruthenium Pincer‐Catalyzed Acylation of Alcohols Using Esters with Liberation of Hydrogen under Neutral Conditions. Advanced Synthesis & Catalysis, 352(18), 3169–3173. Portico.

Authors 3
  1. Boopathy Gnanaprakasam (first)
  2. Yehoshoa Ben‐David (additional)
  3. David Milstein (additional)
References 43 Referenced 76
  1. {'key': 'e_1_2_4_2_2', 'volume-title': 'Comprehensive Organic Synthesis', 'year': '1992'} / Comprehensive Organic Synthesis (1992)
  2. {'key': 'e_1_2_4_3_2', 'volume-title': 'Comprehensive Organic Transformations', 'author': 'Larock R. C.', 'year': '1996'} / Comprehensive Organic Transformations by Larock R. C. (1996)
  3. 10.1002/3527601848
  4. For reviews on transesterifications see:
  5. 10.1021/cr00020a004
  6. 10.1002/3527601848
  7. 10.1021/ar030146d
  8. {'key': 'e_1_2_4_9_2', 'first-page': '985', 'volume': '971', 'author': 'Grasa G. A.', 'year': '2004', 'journal-title': 'Synthesis'} / Synthesis by Grasa G. A. (2004)
  9. 10.1023/B:TOCA.0000013543.96438.1a
  10. 10.1021/cr068372z
  11. For recent contributions regarding catalytic transesterification see:
  12. 10.1016/j.tetlet.2005.01.158
  13. 10.1007/s10562-006-0091-1
  14. {'key': 'e_1_2_4_15_2', 'first-page': '491', 'author': 'Remme N.', 'year': '2007', 'journal-title': 'Synlett'} / Synlett by Remme N. (2007)
  15. 10.1016/j.tetlet.2007.11.008
  16. 10.1021/ja711349r
  17. {'key': 'e_1_2_4_18_2', 'first-page': '605', 'author': 'Inahashi N.', 'year': '2008', 'journal-title': 'Synlett'} / Synlett by Inahashi N. (2008)
  18. 10.1002/ange.200461416
  19. 10.1002/anie.200461416
  20. 10.1039/b910162d
  21. 10.1021/ol8005979
  22. 10.1021/ol702580a
  23. 10.1021/ol0057131
  24. {'key': 'e_1_2_4_24_2', 'first-page': '1659', 'author': 'Iwasaki T.', 'year': '2009', 'journal-title': 'Synlett'} / Synlett by Iwasaki T. (2009)
  25. 10.1021/ol0264760
  26. 10.1021/ol0267228
  27. 10.1021/jo0267551
  28. 10.1021/ja052862b
  29. 10.1039/B613438F
  30. 10.1021/om049716j
  31. 10.1021/ja808893g
  32. 10.1002/ange.200503771
  33. 10.1002/anie.200503771
  34. 10.1126/science.1145295
  35. 10.1002/ange.200907018
  36. 10.1002/anie.200907018
  37. 10.1021/ja066411i
  38. 10.1039/b909852f
  39. 10.1021/ja103130u
  40. 10.1126/science.1168600
  41. All of the ethyl acetate has disappeared; due to its volatility some ethyl acetate might have been lost during reflux.
  42. Excess cyclohexanol remained mostly unreacted under the reaction conditions with a small amount of cyclohexanone being formed.
Dates
Type When
Created 14 years, 8 months ago (Dec. 7, 2010, 11:29 a.m.)
Deposited 1 year, 10 months ago (Oct. 16, 2023, 12:59 p.m.)
Indexed 1 year ago (Aug. 5, 2024, 9:21 p.m.)
Issued 14 years, 8 months ago (Dec. 7, 2010)
Published 14 years, 8 months ago (Dec. 7, 2010)
Published Online 14 years, 8 months ago (Dec. 7, 2010)
Published Print 14 years, 8 months ago (Dec. 17, 2010)
Funders 0

None

@article{Gnanaprakasam_2010, title={Ruthenium Pincer‐Catalyzed Acylation of Alcohols Using Esters with Liberation of Hydrogen under Neutral Conditions}, volume={352}, ISSN={1615-4169}, url={http://dx.doi.org/10.1002/adsc.201000663}, DOI={10.1002/adsc.201000663}, number={18}, journal={Advanced Synthesis & Catalysis}, publisher={Wiley}, author={Gnanaprakasam, Boopathy and Ben‐David, Yehoshoa and Milstein, David}, year={2010}, month=dec, pages={3169–3173} }