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ChemComm
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DOI: 10.1039/C8CC01284A
COMMUNICATION
Journal Name
a. Deuterium-labeling experiment by using CD3OH as reactant
2
3
(a) Q. Yang, G. Shang, W.-Z. Gao, J.-G. Deng and X.-M. Zhang,
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SO2Ph
N
SO2Ph
Me
HN
Pd(OAc)2, (R)-Segphos, Zn(OTf)2
Me
+
CD3OH
H(D)
CF3SO3H, DCE, 4 Å MS, 70
C
14, 4638-4641.
8
5%
1a
3aa-D
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1009; (b) D. Wang and D. Astruc, Chem. Rev., 2015, 115,
b. Transfer hydrogenation reaction by using enantiopure alcohol with a racemic ligand
SO2Ph
N
OH
SO2Ph
HN
Pd(OAc)2, (±)-Segphos, Zn(OTf)2
CF3SO3H, DCE, 4 Å MS, 70
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Rac-3aa
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6
, 5693-5707; (f) P. Roszkowski and Z. Czarnocki, Mini-Rev.
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c. Proposed reaction pass way
PdL*(OAc)2
+
CH3OH
4
SO2Ph
Me
4
5
HN
-
HOAc
3
Zn2+
1770; (c) K. Saito, Y. Shibata, M. Yamanaka and T. Akiyama, J.
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Sugiono, C. Azap, T. Theissmann and M. Bolte, Org. Lett.,
O
H3C
PdL*OAc
CH3OH + HOAc
Me
A
2
005, 7, 3781-3783.
Zn2+
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Deshpande, S. K. Shingote, A. Joseph and A. A. Kelkar, Org.
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SO2Ph
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O
PdL*OAc
CH2
H
PdL*OAc
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D
SO2Ph
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M. Poyatos and E. Peris, ChemCatChem, 2016,
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Kuriakose, K. Vanka and A. A. Kelkar, RSC Adv., 2014,
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N
O
Zn2+
+
(
H
H
AcOL*Pd
H
4
,
C
1a
4
Figure 1 Mechanism study and a proposed reaction path way through
a [Pd-H] hydride intermediate.
2
852.
6
7
(a) H.-Y. Xu, P. Yang, P. Chuanprasit, H. Hirao and J.-R. Zhou,
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In summary, a general and robust strategy of asymmetric
transfer hydrogenation reactions of N-sulfonylimines by using
alcohols were established with palladium/zinc co-catalysts. A
wide range of simple alcohols can serve as effective hydrogen
sources, and successfully delivered various N-sulfonylimines to
its corresponding chiral amines in generally good yields with
excellent enantioselectivities. The present ATH reactions may
provide an effective method for the preparation of various
highly enantioenriched amines.
2
015, 127, 5201-5205; (b) P. Roszkowski, J. K. Maurin and Z.
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We gratefully thank prof. Jianliang Xiao (University of
Liverpool) for his valuble suggestions in the investigation of the
ATH reaction. We thank the National Natural Science Founda-
tion of China (21572198, 21362043, 21302162), the Applied
Basic Research Project of Yunnan Province (2017FA004) and
the Department of Education of Yunnan Province (2017ZDX046,
ZD2015012) for their financial support.
8
9
(a) S. Werkmeister, S. Fleischer, K. Junge and M. Beller,
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Conflicts of interest
8
,
There are no conflicts to declare.
3
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Angew. Chem. Int. Ed., 2016, 55, 9615-9619; Angew. Chem.,
Notes and references
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2 The crystallographic data of 3aa was deposited in the
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| J. Name., 2012, 00, 1-3
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