O rP gl ea na si ce &d Bo i on mo to al e dc juu l sa tr mC ha er mg i ins ts ry
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COMMUNICATION
Journal Name
DOI: 10.1039/D0OB01610A
S. B. Lang, D. R. Heitz and G. A. Molander, ACS Catal., 2017,
In summary, we have developed a Ni/Ir metallaphotoredox
catalysis using the boracene-based alkylborate, oxidatively
quenchable alkyl radical precursor. The hybrid catalysis
enabled the cross-coupling with shorter reaction time, higher
product yield, even under significantly lower irradiances.
According to the reaction analyses, the Ir photoredox catalyst
would enhance the radical generation step with borate.
Angew. Chem. Int. Ed., 2019, 58, 6152-6163. (c) J. K. Matsui,
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, 2563-2575.
8
(a) M. Yuan, Z. Song, S. O. Badir, G. A. Molander and O.
Gutierrez, J. Am. Chem. Soc., 2020, 142, 7225-7234. (b) D. N.
Primer and G. A. Molander, J. Am. Chem. Soc., 2017, 139,
9
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847-9850. (c) R. Alam and G. A. Molander, J. Org. Chem.,
017, 82, 13728-13734. (d) R. Karimi-Nami, J. C. Tellis and G.
A. Molander, Org. Lett., 2016, 18, 2572-2575. (e) D. R. Heitz,
J. C. Tellis and G. A. Molander, J. Am. Chem. Soc., 2016, 138,
Conflicts of interest
1
2715-12718. (f) Y. Yamashita, J. C. Tellis and G. A.
Molander, Proc. Natl. Acad. Sci. U. S. A., 2015, 112, 12026-
2029. (g) D. N. Primer, I. Karakaya, J. C. Tellis and G. A.
1
There are no conflicts to declare.
Molander, J. Am. Chem. Soc., 2015, 137, 2195-2198. (h) J. C.
Tellis, D. N. Primer and G. A. Molander, Science, 2014, 345,
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33-436.
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1
1
1
See Supporting Information for detailed optimization of
reaction conditions.
Acknowledgement
0 We confirmed that the reaction proceeded with comparable
efficiency using longpass filter, Cut-Off Wavelength: 430 nm.
1 We also compared the efficiency of the cross-coupling with
This work was supported by JSPS KAKENHI Grant Number
JP18H01971 to Scientific Research (B), JSPS KAKENHI Grant Number
JP17H06449 (Hybrid Catalysis), Kanazawa University SAKIGAKE
Project 2018, JST, PRESTO Grant Number JPMJPR19T2 (to H.O.),
JSPS KAKENHI Grant Number JP18K05135 to Scientific Research (C),
and TOBE MAKI Foundation (to Y.S.).
3
tBuBF K. See Supporting Information in details.
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