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Synthesis 2020; 52(16): 2330-2336
DOI: 10.1055/s-0040-1707398
DOI: 10.1055/s-0040-1707398
feature
Efficient Heterogeneous Palladium-Catalyzed Transfer Hydrogenolysis of Benzylic Alcohols by Formic Acid
We are grateful for the financial support from the European Union and Mid Sweden University (Mittuniversitetet).Further Information
Publication History
Received: 27 March 2020
Accepted after revision: 28 April 2020
Publication Date:
20 May 2020 (online)
‡ These authors contributed equally to this work
Abstract
An efficient heterogeneous palladium-catalyzed transfer hydrogenolysis of primary, secondary, and tertiary benzylic alcohols using formic acid as hydrogen source has been developed. The resulting hydrocarbon products were obtained in excellent yields. Moreover, the system exhibits high chemoselectivity, reacting only with the hydroxy groups in the presence of other functional groups, and excellent recyclability.
Key words
benzylic alcohols - heterogeneous catalysis - catalytic transfer hydrogenolysis - formic acidSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1707398.
- Supporting Information
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References
- 1 Ranade VS, Prins R. Chem. Eur. J. 2000; 6: 313
- 2 Yasuda M, Onishi Y, Ueba M, Miyai T, Baba A. J. Org. Chem. 2001; 66: 7741
- 3 Muzart J. Tetrahedron 2005; 40: 9423
- 4 Chen H, Lin Y, Chen G, Hu G, Wang L, Vrijmoed LL. P. Chem. Nat. Compd. 2006; 42: 407
- 5 Thakar N, Polder NF, Djanashvili K, Bekkum H, Kapteijn F, Moulijn JA. J. Catal. 2007; 246: 344
- 6 Schlaf M. Dalton Trans. 2006; 39: 4645
- 7 Jian F, Jinbo W, Yafen Z, Haiyan F, Hua C, Xianjun L. Chem. Lett. 2007; 36: 1274
- 8 Jian F, Maolin Y, Hua C, Xianjun L. Prog. Chem. 2007; 19: 651
- 9 Herrmann JM, König B. Eur. J. Org. Chem. 2013; 7017
- 10 Sun Z, Fridrich B, de Santi A, Elangovan S, Barta K. Chem. Rev. 2018; 118: 614
- 11 Fu J, Lym J, Zheng W, Alexopoulos K, Mironenko AV, Li N, Bocoboinik A, Su D, Weber RT, Vlachos DG. Nat. Catal. 2020; 3: 446
- 12 Takada Y, Caner J, Naka H, Saito S. Pure Appl. Chem. 2018; 90: 167
- 13 Musolino MG, Scarpino LA, Mauriello F, Pietropaolo R. Green Chem. 2009; 11: 1511
- 14 Baán Z, Potor A, Cwik A, Hell Z, Keglevich G, Finta Z, Hermecz I. Synth. Commun. 2008; 38: 1601
- 15 Zinovyev S, Shelepchikov A, Tundo P. Appl. Catal., B. 2007; 72: 289
- 16 Feng J, Yang C, Zhang D, Wang J, Fu H, Chen H, Li X. Appl. Catal., A. 2009; 354: 38
- 17 Sawadjoon S, Lundstedt A, Samec JS. ACS Catal. 2013; 3: 635
- 18 Liu X, Lu G, Guo Y, Guo Y, Wang Y, Wang X. J. Mol. Catal. A: Chem. 2006; 252: 176
- 19 Panagiotopoulou P, Vlachos DG. Appl. Catal. A. 2014; 480: 17
- 20 Jae J, Zheng W, Karim AM, Guo W, Lobo RF, Vlachos DG. ChemCatChem 2014; 6: 848
- 21 Yin L, Liebscher J. Chem. Rev. 2007; 107: 133
- 22 Ping EW, Wallace R, Pierson J, Fuller TF, Jones CW. Micropor. Mesopor. Mat. 2010; 132: 174
- 23 Shakeri M, Tai C.-W, Göthelid E, Oscarsson S, Bäckvall J.-E. Chem. Eur. J. 2011; 17: 13269
- 24 Johnston EV, Verho O, Kärkäs MD, Shakeri M, Tai C.-W, Palmgren P, Eriksson K, Oscarsson S, Bäckvall J.-E. Chem. Eur. J. 2012; 18: 12202
- 25 Long W, Brunelli NA, Didas SA, Ping EW, Jones CW. ACS Catal. 2013; 3: 1700
- 26 Engström K, Johnston EV, Verho O, Gustafson KP. J, Shakeri M, Tai C.-W, Bäckvall J.-E. Angew. Chem. Int. Ed. 2013; 52: 14006
- 27 Verho O, Nagendiran A, Johnston EV, Tai C.-W, Bäckvall J.-E. ChemCatChem 2013; 5: 612
- 28 Li M.-B, Yang Y, Rafi A, Oschmann M, Grape ES, Inge K, Córdova A, Bäckvall J.-E. Angew. Chem. Int. Ed. 2020; 59
- 29 Nagendiran A, Pascanu V, Bermejo Gomez A, Gonzalez Miera G, Tai C.-W, Verho O, Martin-Matute B, Bäckvall J.-E. Chem. Eur. J. 2016; 22: 7184
- 30 Volkov A, Gustafson KP, Tai C.-W, Verho O, Bäckvall J.-E, Adolfsson H. Angew. Chem. Int. Ed. 2015; 54: 5122
- 31 Verho O, Gustafson KP. J, Nagendiran A, Tai C.-W, Bäckvall J.-E. ChemCatChem 2014; 6: 3153
- 32 Deiana L, Afewerki S, Palo-Nieto C, Verho S, Johnston EV, Córdova A. Sci. Rep. 2012; 2: 851
- 33 Ma G, Afewerki S, Deiana L, Palo-Nieto C, Liu L, Sun J, Ibrahem I. Angew. Chem. Int. Ed. 2013; 52: 6050
- 34 Deiana L, Jiang Y, Palo-Nieto C, Afewerki S, Incerti-Pradillos CA, Verho O, Tai C.-W, Johnston EV, Córdova A. Angew. Chem. Int. Ed. 2014; 53: 3447
- 35 Deiana L, Ghisu L, Afewerki S, Verho O, Johnston EV, Hedin N, Bacsik Z, Córdova A. Adv. Synth. Catal. 2014; 356: 2485
- 36 Deiana L, Ghisu L, Córdova O, Afewerki S, Zhang R, Córdova A. Synthesis 2014; 46: 1303
- 37 Palo-Nieto C, Afewerki S, Anderson M, Tai C.-W, Berglund P, Córdova A. ACS Catal. 2016; 6: 3932
- 38 Santoro S, Deiana L, Zhao G.-L, Lin S, Himo F, Córdova A. ACS Catal. 2014; 4: 4474
- 39 Zhang D, Liu J, Córdova A, Liao W.-W. ACS Catal. 2017; 7: 7051
- 40 A patent has been approved: Córdova A, Afewerki S, Palo-Nieto C. WO2016066835A1, 2016 , priority date: 2014-10-30
- 41 Icker M, Fricke P, Grell T, Hollenbach J, Auer H, Berger S. Magn. Reson. Chem. 2013; 51: 815
- 42 Buser JY, McFarland AD. Chem. Commun. 2014; 50: 4234
- 43 Lancaster JR, Smilowitz R, Turro NJ, Koberstein JT. Photochem. Photobiol. 2014; 90: 394
- 44 Nyquist R. Appl. Spectrosc. 1991; 45: 1649
- 45 Eisch JJ, Dutta S. Organometallics 2005; 24: 3355