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COMMUNICATION
Journal Name
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Y]* absorption at 560 nm. The result suggested that the
electron transfer from TEOA to [eosin Y]* occurred. According
3
134, 16951. b) D. Srimani, Y. Diskin-Posner, Y. Ben-David, D.
DOI: 10.1039/C5CC08697C
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to the lifetime change as a function of the concentration of
TEOA, the rate constant of the electron transfer was estimated
1
1
8
-1 -1
to be 6.7 × 10 M s (Figure S3,d, e). Further addition of
1
2 a) M. W. van Laren, C. J. Elsevier, Angew. Chem. Int. Ed. 1999,
colloidal Pd nanoparticle aqueous solution into the solution of
•
−
38, 3715. b) M. Armbru
Teschner, Y. Grin, R. Schlo
4745. c) T. Mitsudome, Y. Takahashi, S. Ichikawa, T.
̈
TEOA and eosin Y resulted in a distinct quenching of [eosin Y]
(
̈
Figure S3). The electrons from [eosin Y]•− to colloidal Pd
1
nanoparticle, and the protons releasing from TEOA and H2O
captured by the colloidal Pd nanoparticle could generate Pd-H
species in situ for semihydrogenation.
Mizugaki, K. Jitsukawa, K. Kaneda, Angew. Chem. Int. Ed.
2013, 52, 1481. d) E. D. Slack, C. M. Gabriel, B. H. Lipshutz,
Angew. Chem. Int. Ed. 2014, 53, 14051. e) J. Hori, K. Murata,
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In summary, we have successfully combined visible light
catalysis with transfer hydrogenation to realize efficient and
selective semihydrogenation of alkynes at room temperature
and pressure. Under visible light irradiation for 2 h, good to
excellent yields of alkenes have been achieved. More
interestingly, the visible light induced catalytic transfer
hydrogenation enables coupling photoisomerization of the
generated alkenes, depending on the substituted aryl or alkyl
groups, to produce E-alkenes and Z-alkenes exclusively. The
interesting protocol can accomplish the semihydrogenation in
a cleaner, safer, more efficient and selective manner.
1
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1
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Financial support from the Ministry of Science and Technology
of China (2013CB834804, 2014CB239402 and 2013CB834505),
the National Natural Science Foundation of China (21390404,
1
6
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828. e) C. K. Prier, D. A. Rankic, D. W. C. MacMillan, Chem.
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