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ChemComm
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COMMUNICATION
Journal Name
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Chem., 2009, 11, 1937; (b)X. Li, L. Li, YD. OTaI:n1g0,.1L0.3VZ9i/heCwo9AnCrgtCic,0leL2.O3Cn6lu8innBe,
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Zhang, Org. Lett., 2013, 15, 3690; (b) S. Chen, G. Lu and C. Cai,
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Wang, Z. Huang, X. Leng, H. Zhu, G. Liu and Z. Huang, J. Am.
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Scheme 4. Proposed Mechanism
In summary, a sustainable electrochemical 1,4-reduction of
α, β-unsaturated ketones has been developed. Both of the
hydrogen sources, methanol and ammonium chloride, are
inexpensive and user-friendly. This transformation can be
performed under ambient conditions with facile operation and
is readily scalable. Moreover, it is proven to be compatible
with a wide range of α, β-unsaturated ketones bearing various
functional groups. We believe this reaction should be of
considerable synthetic value in terms of green chemistry.
Further explorations of novel, sustainable organic reactions
using electrochemical methods are currently ongoing in our
laboratory.
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(a) A. P. da Silva, A. C. S. Maia and M. Navarro, Tetrahedron
Lett., 2005, 46, 3233; (b) A. P. da Silva, S. D. C. Mota, L. W.
Bieber and M. Navarro, Tetrahedron, 2006, 62, 5435.
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Electrochem. Commun., 2016, 73, 46.
10 J. Li, L. He, X. Liu, X. Cheng and G. Li, Angew. Chem. Int. Ed.,
2019, 58, 1759.
11 TEMPO is widely applied as an electrochemical mediator to
promote indirect electrolysis and can be easily oxidized at
anode owing to its low oxidation potential. More
information about it can be found in reviews such as ref. 7(b).
The oxidation potential of TEMPO was also measured here
via Cyclic Voltammetry(details in the ESI).
12 Higher d-incorporation than 100% at α position of 12b-d2 is
due to keto–enol tautomerism, a similar observation has
been described in ref. 6(c).
The authors gratefully acknowledge for the financial support
from the National Natural Science Foundation of China (Grant
No. 21672047), SKLUWRE (No. 2018DX02) and The Science and
Technology Plan of Shenzhen (JCYJ20180306172044124).
13 G. Laudadio, N. J. W. Straathof, M. D. Lanting, B. Knoops, V.
Hessel and T. Noël, Green Chem., 2017, 19, 4061.
14 J. H. P. Utley, C. Z. Smith and M. Motevalli, J. Chem. Soc.,
Perkin Trans. 2, 2000, 1053.
Conflicts of interest
There are no conflicts to declare.
Notes and references
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4 | J. Name., 2012, 00, 1-3
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