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of a standard solution of quinoline (117
m
L, 129.2 mg, 1.00 mmol) in
L (0.20 mmol,
1.0 equiv) of a standard solution of 1-phenyl-1-propanol (1)
(6.79 mL, 6.71 g, 50 mmol) in 100 mL toluene, and toluene (620 L)
6011e6014; (b) Nishimura, T.; Onoue, T.; Ohe, K.; Uemura, S. J. Org. Chem.1999, 64,
6750e6755; (c) Stahl, S. S. Angew. Chem., Int. Ed. 2004, 43, 3400e3420; (d) Sig-
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S. Inorg. Chem. 2012, 51, 11898e11909.
10 mL toluene, the used additive (0.50 equiv), 400
m
m
were reacted in analogy to the general procedure in Section 4.2. The
total volume of the reaction mixtures was 2 mL in all experiments.
Workup and analysis were performed as described above, using
para-xylene as GC-standard.
4. (a) Mizoguchi, H.; Uchida, T.; Ishida, K.; Katsuki, T. Tetrahedron Lett. 2009, 50,
ꢀ
3432e3435; (b) Johnston, E. V.; Karlsson, E. A.; Tran, L.-H.; Akermark, B.;
€
Backvall, J.-E. Eur. J. Org. Chem. 2010, 2010, 1971e1976; (c) Babu, B. P.; Endo, Y.;
€
Backvall, J.-E. Chem.dEur. J. 2012, 18, 11524e11527.
5. (a) Jiang, N.; Vinci, D.; Liotta, C. L.; Eckert, C. A.; Ragauskas, A. J. Ind. Eng. Chem.
Res. 2007, 47, 627e631; (b) Lin, L.; Juanjuan, M.; Liuyan, J.; Yunyang, W. J. Mol.
Catal. A: Chem. 2008, 291, 1e4; (c) Lin, L.; Liuyan, J.; Yunyang, W. Catal. Commun.
2008, 9, 1379e1382; (d) Hoover, J. M.; Stahl, S. S. J. Am. Chem. Soc. 2011, 133,
16901e16910; (e) Shen, S.-S.; Kartika, V.; Tan, Y. S.; Webster, R. D.; Narasaka, K.
Tetrahedron Lett. 2012, 53, 986e990.
6. (a) Schultz, M. J.; Sigman, M. S. Tetrahedron 2006, 62, 8227e8241; (b) Par-
meggiani, C.; Cardona, F. Green Chem. 2012, 14, 547e564.
7. Iwasawa, T.; Tokunaga, M.; Obora, Y.; Tsuji, Y. J. Am. Chem. Soc. 2004, 126,
6554e6555.
Acknowledgements
Acknowledgment is made to the Donors of the American
Chemical Society Petroleum Research Fund for partial support of
this research (ACS PRF 52119-DNI3). We also acknowledge Brendan
J. McKeogh for assistance with initial experiments.
8. Schultz, M. J.; Hamilton, S. S.; Jensen, D. R.; Sigman, M. S. J. Org. Chem. 2005, 70,
3343e3352.
Supplementary data
9. Conley, N. R.; Labios, L. A.; Pearson, D. M.; McCrory, C. C. L.; Waymouth, R. M.
Organometallics 2007, 26, 5447e5453.
10. Pearson, D. M.; Conley, N. R.; Waymouth, R. M. Organometallics 2011, 30,
1445e1453.
11. Steinhoff, B. A.; Guzei, I. A.; Stahl, S. S. J. Am. Chem. Soc. 2004, 126,
11268e11278.
Additional experimental procedures and data of further additive
and ligand screenings. Supplementary data associated with this
12. Mueller, J. A.; Goller, C. P.; Sigman, M. S. J. Am. Chem. Soc. 2004, 126, 9724e9734.
13. The amount of oxygen in the vial was approximated to be 0.15 mmol (0.
77 equiv) based on the abundance of oxygen in air (20.95%), the remaining
volume in the vial (18 mL), and the ideal gas law. If the decomposition of the
primary reaction product H2O2 into O2 and H2O is assumed to be quantitative,
only 0.5 equiv of oxygen is needed for the reaction: alcoholþ0.
5O2/ketoneþH2O.
References and notes
1. Corey, E. J.; Schmidt, G. Tetrahedron Lett. 1979, 20, 399e402.
2. Ley, S. V.; Norman, J.; Griffith, W. P.; Marsden, S. P. Synthesis 1994, 1994,
639e666.