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Chemical Science
Page 6 of 7
DOI: 10.1039/C6SC00145A
ARTICLE
Journal Name
Gundala, A. Mari, T. Broja, K. Zeitler and S. J. Connon, Chem.
Commun., 2013, 49, 6510-6512; (i) B. A. Tschaen, J. R.
Schmink and G. A. Molander, Org. Lett., 2013, 15, 500-503;
(j) Y. Zhang, S. C. Born and K. F. Jensen, Org. Proc. Res. Dev.,
2014, 18, 1476-1481; (k) A. M. Whittaker and V. M. Dong,
Angew. Chem. Int. Ed., 2015, 54, 1312-1315.
first, affording an aldehyde, which then enters the same
-
catalytic cycle, with HCO3 replacing OAc-. An aldehyde
1
intermediate was indeed observed by H NMR in the coupling
of 4-methylbenzyl alcohol with MeOH.
5
Recent examples: (a) T. Zweifel, J. V. Naubron and H.
Grützmacher, Angew. Chem. Int. Ed., 2009, 48, 559-563; (b)
K. Kaizuka, H. Miyamura and S. Kobayashi, J. Am. Chem. Soc.,
2010, 132, 15096-15098; (c) H. Miyamura, T. Yasukawa and
Conclusions
In conclusion, we have developed a novel catalytic system for
dehydrogenative cross-coupling of aldehydes with alcohols as
well as cross-coupling of primary alcohols to afford esters with
H2 as the only by-product. The catalytic system shows broad
substrate scope, providing an environmentally friendly
alternative for ester preparation. A dimeric Rh(II) complex was
identified as the active catalyst, which appears to function via
the cooperation of both Rh(II) centres, with the base acting as
a proton shuttle. Detailed mechanistic studies as well as
further application of the dimeric rhodium complex in catalysis
are underway in our laboratory.
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Acknowledgements
This research was supported by the National Natural Science
Foundation of China (21473109), the Program for Changjiang
Scholars and Innovative Research Team in University
(IRT_14R33), and the 111 project (B14041).
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6 | J. Name., 2015, 00, 1-3
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