10.1002/chem.202000251
Chemistry - A European Journal
FULL PAPER
[16] a) S. Gowrisankar, H. Neumann, M. Beller, Angew. Chem. Int. Ed. 2011,
50, 5139-5143; b) I. Fleischer, R. Jennerjahn, D. Cozzula, R. Jackstell,
R. Frankeꢀ, M. Beller, ChemSusChem 2013, 6, 417-420; c) P. M. Kathe,
I. Fleischer, Org. Lett. 2019, 21, 2213-2217.
mechanistic alternative to the previously reported mechanisms
relevant for the transformation of lignin model compounds.
Furthermore, the selective (transfer) reduction of aldehydes by a
Pd/L1 system has been unknown before. The substrate scope of
the described transformation comprises various oxygen-based
leaving groups and both aliphatic and aromatic compounds.
[17] W. Clegg, G. R. Eastham, M. R. J. Elsegood, B. T. Heaton, J. A. Iggo, R.
P. Tooze, R. Whyman, S. Zacchini, J. Chem. Soc., Dalton Trans. 2002,
3300-3308.
[18] J. Dai, W. Ren, H. Wang, Y. Shi, Org. Biomol. Chem. 2015, 13, 8429-
8432.
[19] a) J. Meinwald, S. S. Labana, M. S. Chadha, J. Am. Chem. Soc. 1963,
85, 582-585; b) Z. Wang, in Comprehensive Organic Name Reactions
and Reagents, 2010, pp. 1880-1882.
Acknowledgements
Financial support from DFG (Deutsche Forschungsgemeinschaft,
FL 878/4-1), DAAD (Deutscher Akademischer Austauschdienst,
fellowship P. K.) and the University of Tübingen is gratefully
acknowledged. Regina Oechsner (University of Tübingen) is
thanked for technical assistance in the preparation of 1ae.
[20] a) J. M. Fraile, J. I. García, Z. Hormigón, J. A. Mayoral, C. J. Saavedra,
L. Salvatella, ACS Sustain. Chem. Eng. 2018, 6, 1837-1847; b) M. R.
Sturgeon, S. Kim, K. Lawrence, R. S. Paton, S. C. Chmely, M. Nimlos, T.
D. Foust, G. T. Beckham, ACS Sustain. Chem. Eng. 2014, 2, 472-485.
[21] E. Fischer, A. Speier, Ber. Dtsch. Chem. Ges. 1895, 28, 3252-3258.
[22] a) G. R. Eastham, B. T. Heaton, J. A. Iggo, R. P. Tooze, R. Whyman, S.
Zacchini, Chem. Commun. 2000, 609-610; b) V. Goldbach, L. Falivene,
L. Caporaso, L. Cavallo, S. Mecking, ACS Catal. 2016, 6, 8229-8238.
[23] a) F. Morandini, G. Consiglio, V. Lucchini, Organometallics 1985, 4,
1202-1208; b) N. Almenara, S. Azpeitia, M. A. Garralda, M. A. Huertos,
Dalton Trans. 2018, 47, 16225-16231.
Keywords: homogenous catalysis • palladium • rearrangement •
reduction • tandem reaction
[1]
a) J. Zakzeski, P. C. A. Bruijnincx, A. L. Jongerius, B. M. Weckhuysen,
Chem. Rev. 2010, 110, 3552-3599; b) M. D. Kärkäs, B. S. Matsuura, T.
M. Monos, G. Magallanes, C. R. J. Stephenson, Org. Biomol. Chem.
2016, 14, 1853-1914; c) Z. Sun, B. Fridrich, A. de Santi, S. Elangovan,
K. Barta, Chem. Rev. 2018, 118, 614-678.
[2]
[3]
[4]
[5]
J. M. Nichols, L. M. Bishop, R. G. Bergman, J. A. Ellman, J. Am. Chem.
Soc. 2010, 132, 12554-12555.
M. V. Galkin, C. Dahlstrand, J. S. M. Samec, ChemSusChem 2015, 8,
2187-2192.
K. Chen, J. Schwarz, T. A. Karl, A. Chatterjee, B. König, Chem. Commun.
2019, 55, 13144-13147.
a) B. J. Cox, S. Jia, Z. C. Zhang, J. G. Ekerdt, Polym. Degrad. Stab. 2011,
96, 426-431; b) M. Scott, P. J. Deuss, J. G. de Vries, M. H. G. Prechtl, K.
Barta, Catal. Sci. Technol. 2016, 6, 1882-1891.
[6]
a) R. G. Harms, I. I. E. Markovits, M. Drees, W. A. Herrmann, M. Cokoja,
F. E. Kühn, ChemSusChem 2014, 7, 429-434; b) B. Zhang, C. Li, T. Dai,
G. W. Huber, A. Wang, T. Zhang, RSC Adv. 2015, 5, 84967-84973.
E. Feghali, T. Cantat, Chem. Commun. 2014, 50, 862-865.
N. Drosos, G.-J. Cheng, E. Ozkal, B. Cacherat, W. Thiel, B. Morandi,
Angew. Chem., Int. Ed. 2017, 56, 13377-13381.
[7]
[8]
[9]
E. Feghali, G. Carrot, P. Thuéry, C. Genre, T. Cantat, Energ. Environ.
Sci. 2015, 8, 2734-2743.
[10] B. Ciszek, I. Fleischer, Chem. Eur. J. 2018, 24, 12259-12263.
[11] P. Kathe, I. Fleischer, ChemCatChem 2019, 11, 3343-3354.
[12] a) W. Clegg, M. R. J. Elsegood, G. R. Eastham, R. P. Tooze, X. Lan
Wang, K. Whiston, Chem. Commun. 1999, 1877-1878; b) C. Jimenez
Rodriguez, D. F. Foster, G. R. Eastham, D. J. Cole-Hamilton, Chem.
Commun. 2004, 1720-1721; c) A. J. Rucklidge, G. E. Morris, D. J. Cole-
Hamilton, Chem. Commun. 2005, 1176-1178; d) A. A. Núñez Magro, L.-
M. Robb, P. J. Pogorzelec, A. M. Z. Slawin, G. R. Eastham, D. J. Cole-
Hamilton, Chem. Sci. 2010, 1, 723-730.
[13] B. G. R. Harold A. Wittcoff, Jeffrey S. Plotkin, Industrial Organic
Chemicals, Third Edition, John Wiley & Sons, Inc., 2012.
[14] a) J. A. Mmongoyo, Q. A. Mgani, S. J. M. Mdachi, P. J. Pogorzelec, D. J.
Cole-Hamilton, Eur. J. Lipid Sci. Technol. 2012, 114, 1183-1192; b) J. E.
Mgaya, E. B. Mubofu, Q. A. Mgani, D. B. Cordes, A. M. Slawin, D. J.
Cole-Hamilton, Eur. J. Lipid Sci. Technol. 2015, 117, 190-199; c) J. E.
Mgaya, S. A. Bartlett, E. B. Mubofu, Q. A. Mgani, A. M. Z. Slawin, P. J.
Pogorzelec, D. J. Cole-Hamilton, ChemCatChem 2016, 8, 751-757.
[15] a) Y. Zhu, J. Patel, S. Mujcinovic, W. R. Jackson, A. J. Robinson, Green
Chem. 2006, 8, 746-749; b) F. Stempfle, D. Quinzler, I. Heckler, S.
Mecking, Macromolecules 2011, 44, 4159-4166; c) T. Witt, S. Mecking,
Green Chem. 2013, 15, 2361-2364; d) P. Roesle, L. Caporaso, M.
Schnitte, V. Goldbach, L. Cavallo, S. Mecking, J. Am. Chem. Soc. 2014,
136, 16871-16881; e) S. K. Hess, N. S. Schunck, V. Goldbach, D. Ewe,
P. G. Kroth, S. Mecking, J. Am. Chem. Soc. 2017, 139, 13487-13491.
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