10.1002/chem.201904605
Chemistry - A European Journal
COMMUNICATION
765; e) D. Shen, D. L. Poole, C. C. Shotton, A. F. Kornahrens, M. P.
Healy, T. J. Donohoe, Angew. Chem. Int. Ed. 2015, 54, 1642–1645; f) J.
R. Frost, C. B. Cheong, W. M. Akhtar, D. F. J. Caputo, N. G. Stevenson,
T. J. Donohoe, J. Am. Chem. Soc. 2015, 137, 15664–15667; g) C.
Schlepphorst, B. Maji, F. Glorius, ACS Catal. 2016, 6, 4184–4188; h) L.
Rakers, F. Schäfers, F. Glorius, Chem. - A Eur. J. 2018, 24, 15529–
15532.
Acknowledgements
The work was financially supported by the Russian Science
Foundation (grant # 16-13-10393). NMR studies were performed
with the financial support from Ministry of Science and Higher
Education of the Russian Federation using the equipment of
Center for molecular composition studies of INEOS RAS.
Financial support from the DFG (Heisenberg scholarship to M.K.,
KL 2221/4-1) is gratefully acknowledged.
[4]
We have utilized the reducing power of carbon monoxide in alkylation
reactions of amines, amides and cyanoacetates with aldehydes: a) D.
Chusov, B. List, Angew. Chem. Int. Ed. 2014, 53, 5199-5201; b) P. N.
Kolesnikov, D. L. Usanov, E. A. Barablina, V. I. Maleev, D. Chusov, Org.
Lett. 2014, 16, 5068-5071; c) N. Z. Yagafarov, D. L. Usanov, A. P.
Moskovets, N. D. Kagramanov, V. I. Maleev, D. Chusov, ChemCatChem
2015, 7, 2590-2593; d) A. A. Tsygankov, M. Makarova, D. Chusov,
Mendeleev Commun. 2018, 28, 113-122.
We thank Alexei Tsygankov, Ekaterina Kuchuk, Evgeniya
Podyacheva, Maria Makarova for their support.
[5]
There are precedents of the reductive amination and alkylation using the
water-gas shift reaction. For an excellent recent review about water-gas
shift related reductions see: a) A. Ambrosi, S. E. Denmark, Angew. Chem.
Int. Ed. 2016, 55, 12164-12189. For the use of CO as a component of
syngas see: b) A. Fujio, H. Teruyuki, T. Masato, Chem. Lett. 1990, 19,
765-768. For the closest state-of-the-art examples of water-gas shift
reaction see: c) W. Yoshihisa, S. Yutaro, T. Kunihiko, T. Yoshinobu,
Chem. Lett. 1978, 7, 215-216; d) C. D. Pina, E. Falletta, M. Rossi, M.
Gargano, P. Giannoccaro, R. Ciriminna, M. Pagliaro, Appl. Catal. A: Gen.
2007, 321, 35-39; e) S. E. Denmark, M. Y. S. Ibrahim, A. Ambrosi, ACS
Catal. 2017, 7, 613-630.
Keywords: aldehydes, alpha-alkylation, ketones, reductive
coupling, ruthenium
[1]
For a selection of related transformation of carbonyl compounds, see: L.
Guo, W. Srimontree, C. Zhu, B. Maity, X. Liu, L. Cavallo, M. Rueping,
Nat. Commun. 2019, 10, 1957; b) J. L. Schwarz, F. Schäfers, A.
Tlahuext-Aca, L. Lückemeier, F. Glorius, J. Am. Chem. Soc. 2018, 140,
12705–12709; c) M. Flinker, H. Yin, R. W. Juhl, E. Z. Eikeland, J.
Overgaard, D. U. Nielsen, T. Skrydstrup, Angew. Chem. Int. Ed. 2017,
56, 15910–15915; d) T. L. Andersen, M. W. Frederiksen, K. Domino, T.
Skrydstrup, Angew. Chem. Int. Ed. 2016, 55, 10396–10400; e) J. Rong,
T. Pellegrini, S. R. Harutyunyan, Chem. – A Eur. J. 2016, 22, 3558–3570;
f) M. D. Kosobokov, V. V. Levin, M. I. Struchkova, A. D. Dilman, Org. Lett.
2015, 17, 760–763; g) A. V. Gulevich, V. Helan, D. J. Wink, V. Gevorgyan,
Org. Lett. 2013, 15, 956–959; h) Z. Li, V. Gevorgyan, Angew. Chem. Int.
Ed. 2012, 51, 1225–1227.
[6]
a) K. Asimakopoulos, H. N. Gavala, I. V. Skiadas, Chem. Eng. J. 2018,
348, 732–744; b) B. Molitor, H. Richter, M. E. Martin, R. O. Jensen, A.
Juminaga, C. Mihalcea, L. T. Angenent, Bioresour. Technol. 2016, 215,
386–396.
[7]
[8]
B. P. Bhardwaj, Steel and Iron Handbook; NPCS: Delhi, 2014.
T. Hedner, O. Samulesson, P. Währborg, H. Wadenvik, K.-A. Ung, A. J.
D. Ekbom, Drugs 2004, 64, 2315-2343.
[2]
[3]
a) H. Schönherr, T. Cernak, Angew. Chem. Int. Ed. 2013, 52, 12256-
12267; b) E. J. Barreiro, A. E. Kümmerle, C. A. M. Fraga, Chem. Rev.
2011, 111, 5215-5246.
[9]
A. F. Hill, Angew. Chem. Int. Ed. 2000, 39, 130–133.
[10] (a) R. Stepic, C. R. Wick, V. Strobel, D. Berger, N. Vucemilovic-Alagic,
M. Haumann, P. Wasserscheid, A.-S. Smith, D. M. Smith, Angew. Chem.
Int. Ed. 2019, 58, 741–745; b) T. Bauer, R. Stepic, P. Wolf, F. Kollhoff,
W. Karawacka, C. R. Wick, M. Haumann, P. Wasserscheid, D. M. Smith,
A.-S. Smith, J. Libuda, Catal. Sci. Technol. 2018, 8, 344–357
For some examples of the hydrogen borrowing strategy see: a) G. Yan,
A. J. Borah, L. Wang, M. Yang, Adv. Synth. Catal. 2015, 357, 1333-1350;
b) P. Tundo, M. Musolino, F. Aricò, Green Chem. 2018, 20, 28-85; c) M.
Peña-López, P. Piehl, S. Elangovan, H. Neumann, M. Beller, Angew.
Chem. Int. Ed. 2016, 55, 14967–14971; d) L. K. M. Chan, D. L. Poole, D.
Shen, M. P. Healy, T. J. Donohoe, Angew. Chem. Int. Ed. 2014, 53, 761–
This article is protected by copyright. All rights reserved.