Please do not adjust margins
ChemComm
Page 4 of 5
ARTICLE
Journal Name
Pd(PPh3)2Cl2 (0.02 mol %)
4
SiH2Ph
CMP-1 (20 mg)
PhSiH3
•
7
dioxane, 80 oC, N2
7
DOI: 10.1039/C9CC09387G
1a
2a
Chem. Soc. Rev., 2012, 41, 1845-1866; (c) J. D. Sellars, P. G.
Steel and M. J. Turner, Chem. Commun., 2006, 22, 2385-2387.
(a) R. Moser, T. Nishikata and B. H. Lipshutz, Org. Lett., 2010,
12, 28-31; (b) D. J. Vyas and M. Oestreich, Angew. Chem., Int.
Ed., 2010, 49, 8513-8515.
(a) H. Wen, K. Wang, Y. Zhang, G. Liu and Z. Huang, ACS Catal.,
2019, 9, 1612-1618; (b) H. L. Sang, S. Yu and S. Ge, Chem. Sci.,
2018, 9, 973-978; (c) J. Y. Wu, B. N. Stanzl, and T. Ritter, J. Am.
Chem. Soc., 2010, 132, 13214-13216.
(a) Z. D. Miller, W. Li, T. R. Belderrain and J. Montgomery, J.
Am. Chem. Soc., 2013, 135, 15282-15285; (b) Z. D. Miller, R.
Dorel and J. Montgomery, Angew. Chem., Int. Ed., 2015, 54,
9088-9091.
5
6
runs
7
Figure 4. Studies on recycling of CMP-1 for the Hydrosilylation of 1-
Octylallene and PhSiH3.
8
9
M. Kidonakis and M. Stratakis, Org. Lett., 2015, 17, 4538-
4541.
(a) Y.-H. Xu, L.-H. Wu, J. Wang and T.-P. Loh, Chem. Commun.,
2014, 50, 7195-7197; (b) S. Pashikanti, J. A. Calderone, M. K.
Nguyen, C. D. Sibley and W. L. Santos, Org. Lett., 2016, 18,
2443-2446.
Conclusions
In summary, we have developed a conjugated microporous
polymer with pyridines containing adjacent C≡C bonds as the
ligand unit. The resultant Pd-CMP-1 was first applied as a highly
efficient heterogeneous catalytic system for the Pd-catalyzed
regioselective allene hydrosilylation towards a wide scope of
allenes to produce branched allylsilanes. The ligand units of the
polymer, along with the confinement effect of the porous
structure, jointly regulated the regioselectivity. The parts-per-
million (ppm) levels of Pd, coordinated with the recyclable
heterogeneous ligand, shows promise for industrial application.
This work opens a new front of using CMP as an intriguing
platform for developing highly efficient catalysts in the control
of the regioselectivities in allene hydrosilylation.
10 S. Asako, S. Ishikawa and K. Takai, ACS Catal., 2016, 6, 3387-
3395.
11 (a) C. Wang, W. J. Teo and S. Ge, Nat. Commun., 2017, 8, 2258-
2266; (b) Z. Yang, D. Peng, X. Du, Z. Huang and S. Ma, Org.
Chem. Front., 2017, 4, 1829-1832.
12 Z. D. Miller and J. Montgomery, Org. Lett., 2014, 16, 5486-
5489.
13 H. Tafazolian and J. A. R. Schmidt, Chem. Commun., 2015, 51,
5943-5946.
14 (a) Y. Kou, Y. Xu, Z. Guo and D. Jiang, Angew. Chem., Int. Ed.,
2011, 50, 8753-8757; (b) F. Xu, X. Chen, Z. Tang, D. Wu, R. Fu
and D. Jiang, Chem. Commun., 2014, 50, 4788-4790.
15 (a) X. Liu, Y. Xu and D. Jiang, J. Am. Chem. Soc., 2012, 134,
8738-8741; (b) K. Wu, J. Guo and C. Wang, Chem. Commun.,
2014, 50, 695-697; (c) C. Gu, N. Huang, J. Gao, F. Xu, Y. Xu and
D. Jiang, Angew. Chem., Int. Ed., 2014, 53, 4850-4855.
16 (a) A. Li, R.-F. Lu, Y. Wang, X. Wang, K.-L. Han and W.-Q. Deng,
Angew. Chem., Int. Ed., 2010, 49, 3330-3333; (b) Q. Chen, M.
Luo, P. Hammershoj, D. Zhou, Y. Han, B. W. Laursen, C.-G. Yan
and B.-H. Han, J. Am. Chem. Soc., 2012, 134, 6084-6087.
17 (a) Y. Xu, L. Chen, Z. Guo, A. Nagai and D. Jiang, J. Am. Chem.
Soc., 2011, 133, 17622-17625; (b) L. Chen, Y. Honsho, S. Seki
and D. Jiang, J. Am. Chem. Soc., 2010, 132, 6742-6748.
18 (a) L. Chen, Y. Yang, Z. Guo, and D. Jiang, Adv. Mater., 2011,
23, 3149–3154; (b) J.-X. Jiang, C. Wang, A. Laybourn, T. Hasell,
R. Clowes, Y. Z. Khimyak, J. Xiao, S. J. Higgins, D. J. Adams and
A. I. Cooper, Angew Chem., Int. Ed., 2011, 50, 1072-1075; (c)
Y. Xu, S. Jin, H. Xu, A. Nagai and D. Jiang, Chem. Soc. Rev., 2013,
42, 8012-8031; (d) L. Chen, Y. Yang, and D. Jiang, J. Am. Chem.
Soc., 2010, 132, 9138-9143; (e) J.-X. Jiang, Y. Li, X. Wu, J. Xiao,
D. J. Adams and A. I. Cooper, Macromolecules, 2013, 46, 8779-
8783; (f) W. Zhang, J. Tang, W. Yu, Q. Huang, Y. Fu, G. Kuang,
C. Pan and G. Yu, ACS Catal., 2018, 8, 8084-8091; (g) Y.-B. Zhou
and Z.-P. Zhan, Chem. - Asian J., 2018, 13, 9-19.
19 (a) Y.-B. Zhou, Y.-Q. Wang, L.-C. Ning, Z.-C. Ding, W.-L. Wang,
C.-K. Ding, R.-H. Li, J.-J. Chen, X.-Lu, Y.-J. Ding and Z.-P. Zhan,
J. Am. Chem. Soc., 2017, 139, 3966-3969; (b) R.-H. Li, Z.-C.
Ding, C.-Y. Li, J.-J. Chen, Y.-B. Zhou, X.-M. An, Y.-J. Ding and Z.-
P. Zhan, Org. Lett., 2017, 19, 4432-4435; (c) R. Li, B. C. Ma, W.
Huang, L. Wang, D. Wang, H. Lu, K. Landfester and K. A. I.
Zhang, ACS Catal., 2017, 7, 3097-3101.
20 (a) Q. Sun, Z. Dai, X. Liu, N. Sheng, F. Deng, X. Meng, and F.-S.
Xiao, J. Am. Chem. Soc. 2015, 137, 5204-5209; (b) Q. Sun, M.
Jiang, Z. Shen, Y. Jin, S. Pan, L. Wang, X. Meng, W. Chen, Y.
Ding, J. Li and F.-S. Xiao, Chem. Commun., 2014, 50, 11844-
11847.
Conflicts of interest
There are no conflicts to declare.
Acknowledgements
We are grateful to the National Natural Science Foundation of
China (No. 21772166 and 91845101), the Chinese Universities
Scientific Fund (No. 20720190132) and NFFTBS (No. J1310024).
Notes and references
1
(a) W.-H. Li, C.-Y. Li, H.-Y. Xiong, Y. Liu, W.-Y. Huang, G.-J. Ji, Z.
Jiang, H.-T. Tang, Y.-M. Pan and Y.-J. Ding, Angew. Chem., Int.
Ed., 2019, 58, 2448-2453; (b) K. Kaneda and T. Mizugaki,
Green Chem., 2019, 21, 1361-1389; (c) R.-H. Li, X.-M. An, Y.
Yang, D.-C. Li, Z.-L. Hu and Z.-P. Zhan, Org. Lett., 2018, 20,
5023-5026; (d) L. Liu and A. Corma, Chem. Rev., 2018, 118,
4981-5079; (e) W.-H. Li, C.-Y. Li, Y. Li, H.-T. Tang, H.-S. Wang,
Y.-M. Pan and Y.-J. Ding, Chem. Commun., 2018, 54, 8446-
8449.
2
3
(a) X.-C. Wang, W. Gong, L.-Z. Fang, R.-Y. Zhu, S. Li, K. M. Engle
and J.-Q. Yu, Nature, 2015, 519, 334-338; (b) G.-Q. Chen, B.-J.
Lin, J.-M. Huang, L.-Y. Zhao, Q.-S. Chen, S.-P. Jia, Q. Yin and X.
Zhang, J. Am. Chem. Soc., 2018, 140, 8064-8068.
(a) I. Fleming, A. Barbero and D. Walter, Chem. Rev., 1997, 97,
2063-2192; (b) S. E. Denmark and J. H.-C. Liu, Angew. Chem.,
Int. Ed., 2010, 49, 2978-2986; (c) A. Barbero and F. J. Pulido,
Acc. Chem. Res., 2004, 37, 817-825.
4 | J. Name., 2012, 00, 1-3
This journal is © The Royal Society of Chemistry 20xx
Please do not adjust margins