Communication
ChemComm
4 (a) D. Li, H. Zhang and Y. Wang, Chem. Soc. Rev., 2013, 42, 8416;
(b) Y.-L. Rao, H. Amarne and S. Wang, Coord. Chem. Rev., 2012,
256, 759; (c) N. Boens, V. Leen and W. Dehaen, Chem. Soc. Rev., 2012,
41, 1130; (d) A. Loudet and K. Burgess, Chem. Rev., 2007, 107, 4891.
5 (a) X. F. Wang, S. S. Yu, C. Wang, D. Xue and J. Xiao, Org. Biomol. Chem.,
2016, 14, 7028; (b) X. Guo, X. Li, X.-C. Liu, P. Li, Z. Yao, J. Li, W. Zhang,
J.-P. Zhang, D. Xue and R. Cao, Chem. Commun., 2018, 54, 845.
6 For a recent summary, L.-C. Campeau and N. Hazari, Organometallics,
2019, 38, 3.
7 For reviews on this topic, (a) J. A. Milligan, J. P. Phelan, S. O. Badir
and G. A. Molander, Angew. Chem., Int. Ed., 2019, 58, 6152;
(b) J. Twilton, C. Le, P. Zhang, M. H. Shaw, R. W. Evans and
D. W. C. MacMillan, Nat. Rev. Chem., 2017, 1, 0052; (c) Y.-Y. Gui,
L. Sun, Z.-P. Lu and D.-G. Yu, Org. Chem. Front., 2016, 3, 522;
(d) M. D. Levin, S. Kim and F. D. Toste, ACS Cent. Sci., 2016,
2, 293; (e) K. L. Skubi, T. R. Blum and T. P. Yoon, Chem. Rev.,
2016, 116, 10035; ( f ) M. N. Hopkinson, A. Tlahuext-Aca and
F. Glorius, Acc. Chem. Res., 2016, 49, 2261; (g) D. C. Fabry and
M. Rueping, Acc. Chem. Res., 2016, 49, 1969; (h) C. K. Prier,
D. A. Rankic and D. W. MacMillan, Chem. Rev., 2013, 113, 5322;
(i) J. C. Tellis, C. B. Kelly, D. N. Primer, M. Jouffroy, N. R. Patel and
G. A. Molander, Acc. Chem. Res., 2016, 49, 1429.
metallaphotoredox catalysed C–O cross-coupling reactions.
A wide array of O-based nucleophiles, including carboxylic
acids, water, alcohols, were effectively coupled with (hetero)aryl
halides under this operationally simple dual catalytic system,
affording the corresponding product in moderate to excellent
yields. We anticipate this organoboron photocatalyst to be an
inexpensive, sustainable complement to the existing photoca-
talysts in metallaphotoredox reactions. Further applications of
these compounds are ongoing in our laboratory.
We thank Prof. Ruben Martin in ICIQ, and Prof. Pengfei Li
in FIST, XJTU for their critical reading and suggestions. Finan-
cial support by the National Natural Science Foundation of
China (No. 21963010), Shihezi University (CXRC201602), and
China Scholarship Council is acknowledged. C. D. thanks
European Union’s Horizon 2020 under the Marie Curie PREB-
IST grant agreement 754558.
8 For a very recent summary, C. Cavedon, P. H. Seeberger and
B. Pieber, Eur. J. Org. Chem., 2020, 1379.
9 J. A. Terrett, J. D. Cuthbertson, V. W. Shurtleff and D. W. C. MacMillan,
Nature, 2015, 524, 330.
10 E. R. Welin, C. Le, D. M. Arias-Rotondo, J. K. McCusker and
D. W. C. MacMillan, Science, 2017, 355, 380.
Conflicts of interest
There are no conflicts to declare.
11 For other dual nickel/photocatalysis for C–O construction using Ir-
based photocatalysts: (a) H. Ye, C. Xiao, Q.-Q. Zhou, P. G. Wang and
W.-J. Xiao, J. Org. Chem., 2018, 83, 13325; (b) Q.-Q. Zhou, F.-D. Lu,
D. Liu, L.-Q. Lu and W.-J. Xiao, Org. Chem. Front., 2018, 5, 3098.
Notes and references
1 For reviews, (a) L. Buzzetti, G. E. M. Crisenza and P. Melchiorre,
Angew. Chem., Int. Ed., 2019, 58, 3730; (b) R. C. McAtee, E. J. McClain
and C. R. J. Stephenson, Trends Chem., 2019, 1, 111; (c) L. Marzo, 12 J. Lu, B. Pattengale, Q. Liu, S. Yang, W. Shi, S. Li, J. Huang and
S. K. Pagire, O. Reiser and B. Konig, Angew. Chem., Int. Ed., 2018, J. Zhang, J. Am. Chem. Soc., 2018, 140, 13719.
57, 10034; (d) M. D. Karkas, J. A. Porco and C. R. J. Stephenson, Chem. 13 D. L. Zhu, H. X. Li, Z. M. Xu, H. Y. Li, D. J. Young and J. P. Lang, Org.
Rev., 2016, 116, 9683; (e) M. H. Shaw, J. Twilton and D. W. C. MacMillan, Chem. Front., 2019, 6, 2353.
J. Org. Chem., 2016, 81, 6898; ( f ) D. M. Schultz and T. P. Yoon, Science, 14 L. Yang, Z. Huang, G. Li, W. Zhang, R. Cao, C. Wang, J. Xiao and
2014, 343, 1239176; (g) J. Xuan and W. J. Xiao, Angew. Chem., Int. Ed., D. Xue, Angew. Chem., Int. Ed., 2018, 57, 1968.
2012, 51, 6828; (h) J. M. R. Narayanam and C. R. J. Stephenson, Chem. 15 H. Lee, N. C. Boyer, Q. Deng, H.-Y. Kim, T. K. Sawyer and N. Sciammetta,
Soc. Rev., 2011, 40, 102; (i) Y. Chen, L.-Q. Lu, D.-G. Yu, C.-J. Zhu and Chem. Sci., 2019, 10, 5073.
W.-J. Xiao, Sci. China: Chem., 2019, 62, 24; ( j) D. Petzold, M. Giedyk, 16 For heterogeneous dual nickel/photocatalysis for C–O construction,
¨
¨
¨
A. Chatterjee and B. Konig, Eur. J. Org. Chem., 2020, 1193.
(a) C. Cavedon, A. Madani, P. H. Seeberger and B. Pieber, Org. Lett.,
2019, 21, 5331; (b) B. Pieber, J. A. Malik, C. Cavedon, S. Gisbertz,
A. Savateev, D. Cruz, T. Heil, G. Zhang and P. H. Seeberger, Angew.
Chem., Int. Ed., 2019, 58, 9575; (c) Y. Y. Liu, D. Liang, L. Q. Lu and
W. J. Xiao, Chem. Commun., 2019, 55, 4853. For a recent UV-promoted
nickel-catalysed C–O coupling without any photosensitizer: (d) L. Yang,
H.-H. Lu, C.-H. Lai, G. Li, W. Zhang, R. Cao, F. Liu, C. Wang, J. Xiao and
D. Xue, Angew. Chem., Int. Ed., 2020, DOI: 10.1002/anie.202003359.
2 C. B. Kelly, N. R. Patel, D. N. Primer, M. Jouffroy, J. C. Tellis and
G. A. Molander, Nat. Protoc., 2017, 12, 472.
3 For reviews on cheap metals-based photocatalysts, (a) B. M. Hockin,
C. Li, N. Robertson and E. Zysman-Colman, Catal. Sci. Technol.,
2019, 9, 889; (b) A. Hossain, A. Bhattacharyya and O. Reiser, Science,
2019, 364, eaav9713; (c) M. Parasram and V. Gevorgyan, Chem. Soc.
Rev., 2017, 46, 6227For
a review on organic photocatalysts,
(d) N. A. Romero and D. A. Nicewicz, Chem. Rev., 2016, 116, 10075For 17 (a) D. M. Arias-Rotondo and J. K. McCusker, Chem. Soc. Rev., 2016,
recent achievements on metal-free photocatalytic reactions, (e) M. C. Fu,
R. Shang, B. Zhao, B. Wang and Y. Fu, Science, 2019, 363, 1429;
45, 5803For a recent unified reaction platform based on Ir catalysis,
(b) R. A. Escobar and J. Johannes, Chem. – Eur. J., 2020, 26, 5168.
( f ) I. Ghosh, J. Khamrai, A. Savateev, N. Shlapakov, M. Antonietti and 18 Q. Q. Zhou, Y. Q. Zou, L. Q. Lu and W. J. Xiao, Angew. Chem., Int. Ed.,
¨
B. Konig, Science, 2019, 365, 360.
2019, 58, 1586.
Chem. Commun.
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