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.
References
43
Referenced
76
{'key': 'e_1_2_4_2_2', 'volume-title': 'Comprehensive Organic Synthesis', 'year': '1992'}
/ Comprehensive Organic Synthesis (1992){'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)10.1002/3527601848
- For reviews on transesterifications see:
10.1021/cr00020a004
10.1002/3527601848
10.1021/ar030146d
{'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)10.1023/B:TOCA.0000013543.96438.1a
10.1021/cr068372z
- For recent contributions regarding catalytic transesterification see:
10.1016/j.tetlet.2005.01.158
10.1007/s10562-006-0091-1
{'key': 'e_1_2_4_15_2', 'first-page': '491', 'author': 'Remme N.', 'year': '2007', 'journal-title': 'Synlett'}
/ Synlett by Remme N. (2007)10.1016/j.tetlet.2007.11.008
10.1021/ja711349r
{'key': 'e_1_2_4_18_2', 'first-page': '605', 'author': 'Inahashi N.', 'year': '2008', 'journal-title': 'Synlett'}
/ Synlett by Inahashi N. (2008)10.1002/ange.200461416
10.1002/anie.200461416
10.1039/b910162d
10.1021/ol8005979
10.1021/ol702580a
10.1021/ol0057131
{'key': 'e_1_2_4_24_2', 'first-page': '1659', 'author': 'Iwasaki T.', 'year': '2009', 'journal-title': 'Synlett'}
/ Synlett by Iwasaki T. (2009)10.1021/ol0264760
10.1021/ol0267228
10.1021/jo0267551
10.1021/ja052862b
10.1039/B613438F
10.1021/om049716j
10.1021/ja808893g
10.1002/ange.200503771
10.1002/anie.200503771
10.1126/science.1145295
10.1002/ange.200907018
10.1002/anie.200907018
10.1021/ja066411i
10.1039/b909852f
10.1021/ja103130u
10.1126/science.1168600
- All of the ethyl acetate has disappeared; due to its volatility some ethyl acetate might have been lost during reflux.
- 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) |
@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} }