Chinese Journal of Organic Chemistry >
Potassium Phenyltrifluoroborate-Catalyzed Reduction of Aldehydes and Ketones into Alcohol with Silanes
Received date: 2018-10-11
Revised date: 2018-12-12
Online published: 2019-01-18
Supported by
Project supported by the State Key Laboratory of Fine Chemicals (Panjin) (No. JH2014009) and the Fundamental Research Funds for the Central Universities.
The selective reduction of carbonyl group with organosilane as reducing agent was studied with methanol as a solvent under the action of 2.5 mol% C6H5BF3K and 2.2 epuiv. (EtO)3SiH. The target products were obtained in medium to high yield. This method shows good selectivity and provides a new method for carbonyl reduction.
Liu Jianhui , Wang Xingyang . Potassium Phenyltrifluoroborate-Catalyzed Reduction of Aldehydes and Ketones into Alcohol with Silanes[J]. Chinese Journal of Organic Chemistry, 2019 , 39(5) : 1411 -1416 . DOI: 10.6023/cjoc201810010
[1] Carey, J.-S.; Laffan, D.; Mike, C. T.; Williamsd, T. Org. Biomol. Chem. 2006, 4, 2337.
[2] Jagdale, A.-R.; Paraskar, A.-S.; Sudalai, A. Synthesis, 2009, 660.
[3] Wei, W.; Dai, X.-J.; Wang, H.; Li, C.-C.; Li, C.-J. Chem. Sci. 2017, 8, 8193.
[4] (a) Peng, D.-J.; Zhang, Y.-L.; Du, X.-Y.; Zhang, D.; Leng, X.-B.; Walter, M.-D.; Huang, Z. J. Am. Chem. Soc. 2013, 135, 19154.
(b) Huckaba, A.-J.; Keith Hollis, T.; Reilly, S.-W. Organometallics 2013, 32, 6248.
(c) Bornschein, C.; Werkmeister, S.; Junge, K.; Beller, M. New J. Chem. 2013, 37, 2061.
(d) Das, S.; Li, Y.-H.; Junge, K.; Beller, M. Chem. Commun. 2012, 48, 10742.
(e) Enthaler, S.; Schröder, K.; Inoue, S.; Eckhardt, B.; Junge, K.; Beller, M.; Driess, M. Eur. J. Org. Chem. 2010, 25, 4893.
[5] (a) Ojima, I.; Nihonyanagi, M.; Nagai, Y.; J. Chem. Soc., Chem. Commun. 1972, 27, 938.
(b) Ojima, I.; Kogure, T.; Nihonyanagi, M.; Nagai, Y. Bull. Chem. Soc. Jpn. 1972, 45, 3506.
[6] Kobayashi, Y.; Takahisa, E.; Nakano, M.; Watatani, K. Tetrahedron 1997, 53, 1627.
[7] Srivari, C.; Reddy, C. R.; Babu, B. N. J. Org. Chem. 2002, 67, 9080.
[8] Motoyama, Y.; Mitsui, K.; Ishida, T.; Nagashima, H. J. Am. Chem. Soc. 2005, 127, 13150.
[9] Hanada, S.; Tsutsumi, E.; Motoyama, Y.; Nagashima, H. J. Am. Chem. Soc. 2009, 131, 15032.
[10] Roy, S. R.; Sau, S. C.; Mandal, S.-K. J. Org. Chem. 2014, 79, 9150.
[11] Bernando, J.-R.; Florindo, P. R.; Wolff, M.; Machura, B.; Fernandes, A.-C. Tetrahedron Lett. 2015, 56, 414.
[12] Kochi, J.-K.; Hammond, G.-S. J. Am. Chem. Soc. 1953, 75, 3443.
[13] Castle, R.-N; Riebsomer, J.-L. J. Org. Chem. 1955, 21, 142.
[14] Praill, P. F. G. J. Chem. Soc. 1957, 3162.
[15] Naimi-Jama, M. R.; Mokhtari, J.; Dekamin, M.-G.; Kaupp, G. Eur. J. Org. Chem. 2009, 5, 3567.
[16] Williams, G.; Clark, D. J. J. Chem. Soc. 1956, 1304.
[17] Meier, C.; Clercqb, E. D.; Balzarinib, J. Eur. J. Org. Chem. 1998, 837.
[18] Ashley, J. N.; Barber, H. J.; Ewins, A. J.; Newbery, G.; Self, A. D. H. J. Chem. Soc., 1942, 103.
[19] Errede, L. A.; Hopwood Jr, S. L. J. Am. Chem. Soc. 1957, 79, 6507.
[20] Rhoad, M.-J.; Flory, P.-J. J. Am. Chem. Soc. 1950, 72, 2216.
[21] Tian, H.-N.; Yang, X. H.; Chen, R.-K.; Zhang, R.; Hagfeldt, A.; Sun, L.-C. J. Phys. Chem. C. 2008, 112, 11023.
[22] Chan, F.-L. Anal. Chirn. Acta 1967, 37, 391.
[23] Kumari, P.; Shive M, P.; Chauhan, S. Chem. Commun. 2009, 20, 6397.
[24] Stewart, B.-B.; Smith, H.-A. J. Am. Chem. Soc. 1957, 79, 5457.
/
〈 |
|
〉 |