4
Tetrahedron
Schrock, R. R.; Osborn, J. A. J. Am. Chem. Soc. 1976,
13. Tlili, A.; Schranck, J.; Neumann, H.; Beller, M. Chem.
Eur. J. 2012, 18, 15935-15939.
14. Casey, C. P.; Guan, H. J. Am. Chem. Soc. 2007, 129, 5816-
5817.
15. For selected publications, Knölker iron complex in
reduction reactions, see: a) Casey, C. P.; Guan, H. J. Am.
Chem. Soc. 2009, 131, 2499-2507; b) Zhou, S.; Fleischer,
S.; Junge, K.; Beller, M. Angew. Chem. Int. Ed. 2011, 50,
5120-5124; c) Pagnoux-Ozherelyeva, A.; Pannetier, N.;
Mbaye, M. D.; Gaillard, S.; Renaud, J. L. Angew. Chem.
Int. Ed. 2012, 51, 4976-4980.
16. For enantioselective reductions of C=O bonds, see: a)
Berkessel, A.; Reichau, S.; van der Hçh, A.; Leconte, N.;
Neuddçrfl, J.-M. Organometallics 2011, 30, 3880-3887; b)
Hopewell, J. P.; Martins, J. E. D.; Johnson, T. C.; Godfrey,
J.; Wills, M. Org. Biomol. Chem. 2012, 10, 134-145; c)
Sonnenberg, J. F.; Coombs, N.; Dube, P. A.; Morris, R. H.
J. Am. Chem. Soc. 2012, 134, 5893-5899; d) Sues, P. E.;
Lough, A. J.; Morris, R. H. Organometallics 2011, 30,
4418-4431; e) Lagaditis, P. O.; Lough, A. J.; Morris, R. H.
J. Am. Chem. Soc. 2011, 133, 9662-9665; f) Inagaki, T.;
Ito, A.; Ito, J.-I.; Nishiyama, H. Angew. Chem. Int. Ed.
2010, 49, 9384-9387; g) Inagaki, T.; Phong, L. T.; Furuta,
A.; Ito, J.; Nishiyama, H. Chem. Eur. J. 2010, 16, 3090-
3096; h) Nishiyama, H.; Furuta, A. Chem. Commun. 2007,
760-762; i) Furuta, A.; Nishiyama, H. Tetrahedron Lett.
2008, 49, 110-113; j) Shaikh, N. S.; Enthaler, S.; Junge, K.;
Beller, M. Angew. Chem. Int. Ed. 2008, 47, 2497-2501; k)
Langlotz, B. K.; Wadepohl, H.; Gade, L. H. Angew. Chem.
Int. Ed. 2008, 47, 4670-4674.
98, 2143-2147; f) Schrock, R. R.; Osborn, J. A. J. Am.
Chem. Soc. 1976, 98, 4450-4455; g) Brown, J. M.; Angew.
Chem. Int. Ed. 1987, 26, 190-203; h) Evans, D. A.;
Morrissey, M. M. J. Am. Chem. Soc. 1984, 106, 3866-
3868.
6. a) Crabtree, R. H.; Felkin, H.; Morris, G. E. J. Organomet.
Chem. 1977, 141, 205-215; b) Crabtree, R. H. Acc. Chem.
Res. 1979, 12, 331-337; c) Wstenberg, B.; Pfaltz, A. Adv.
Synth. Catal. 2008, 350, 174-178; d) Smidt, S. P.;
Zimmermann, N.; Studer, M.; Pfaltz, A. Chem. Eur. J.
2004, 10, 4685-4693; e) Suggs, J. W.; Cox, S. D.;
Crabtree, R. H.; Quirk, J. M. Tetrahedron Lett. 1981, 22,
303-306.
7. a) Nagayama, K.; Shimizu, I.; Yamamoto, A. Chem. Lett.
1998, 1143-1144; b) van Laren, M.W.; Elsevier, C. J.
Angew. Chem. Int. Ed. 1999, 38, 3715-3717; c) Hauwert,
P.; Maestri, G.; Sprengers, J.W.; Catellani, M.; Elsevier,
C. J. Angew. Chem. Int. Ed. 2008, 47, 3223-3226.
8. a) Casey, C. P.; Guan, H. J. Am. Chem. Soc. 2007, 129,
5816-5817; b) Langer, R.; Leitus, G.; David, Y. B.;
Milstein, D. Angew. Chem. Int. Ed. 2011, 50, 2120-2124;
c) Bart, S. C.; Lobkovsky, E.; Chirik, P. J. J. Am. Chem.
Soc. 2004, 126, 13794-13807; d) Daida, E. J.; Peters, J. C.
Inorg. Chem. 2004, 43, 7474-7485; e) Zhang, G.; Scott, B.
L.; Hanson, S. K. Angew. Chem. Int. Ed. 2012, 51, 12102-
12106. f) Driller, K. M.; Prateeptongkum, S.; Jackstell, R.;
Beller, M. Angew. Chem. Int. Ed. 2011, 50, 537-541.
9. Liu, M.; Zhou, F.; Jia, Z.; Li, C.-J. Org. Chem. Front.
2014, 1, 161-166.
10. a) Welch, G. C.; Juan, R. R. S.; Masuda, J. D.; Stephan, D.
W. Science 2006, 314, 1124-1126; b) Chase, P. A.; Jurca,
T.; Stephan, D. W. Chem. Commun. 2008, 1701-1703; c)
Spies, P.; Schwendemann, S.; Lange, S.; Kehr, G.;
Frçhlich, R.; Erker, G.; Angew. Chem. Int. Ed. 2008, 47,
7543-7546; d) Chase, P. A.; Welch, G. C.; Jurca, T.;
Stephan, D. W. Angew. Chem. Int. Ed. 2007, 46, 8050-
8053; e) Mahdi, T.; Heiden, Z. M.; Grimme, S.; Stephan,
D. W. J. Am. Chem. Soc. 2012, 134, 4088-4091.
11. For selected an representative review on iron catalysis, see
: Bolm, C.; Legros, J.; Paith, J. L.; Zani, L. Chem. Rev.
2004, 104, 6217-6254.
12. For selected recent examples, see: a) Bhattacharya, P.;
Krause, J.; Guan, H. Organometallics 2011, 30, 4720-
4729; b) Plank, T. N.; Drake, J. L.; Kim, D. K.; Funk, T.
W. Adv. Synth. Catal. 2012, 354, 597-601; c) Buitrago, E.;
Tinnis, F.; Adolfsson, H. Adv. Synth. Catal. 2012, 354,
217-222; d) Mikhailine, A.; Morris, R. H. Inorg. Chem.
2010, 49, 11039-11044.
17. Reduction of Benzaldehyde to Benzylalcohol: Knölker
iron complex 2a (3 mol%, 12.6 mg), paraformaldehyde
(300 mg, 10 mmol), and Na2CO3 (106 mg, 1 mmol, 1.0
equiv.) and a stirring bar were charged in a pressure tube
and flushed with argon. DMSO (1.0 mL), degassed water
(1.0 mL) and benzaldehyde (1 mmol) were added under an
argon atmosphere to the pressure tube with a syringe. The
pressure tube was placed in oil and heated at 120 °C for 24
h, then cooled to room temperature. The reaction mixture
was neutralized with HCl (1M) and stirred for 30 min. After
extraction with EtOAc for 3 times), the combined organic
layers were dried over MgSO4. The crude product was
purified by column chromatography (Heptane/EtOAc:
70:30). The reaction was cooled to room temperature and
hexadecane (100 µL) was added as a GC internal standard.
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