Communication
ChemComm
(d) A. C. Brezny and C. R. Landis, Acc. Chem. Res., 2018, 51, 2344;
(e) F. Hebrard and P. Kalck, Chem. Rev., 2009, 109, 4272;
¨
( f ) P. Eilbracht, L. Barfacker, C. Buss, C. Hollmann, B. E. Kitsos-
Rzychon, C. L. Kranemann, T. Rische, R. Roggenbuck and
A. Schmidt, Chem. Rev., 1999, 99, 3329; (g) A. Gual, C. Godard,
´
S. Castillon and C. Claver, Tetrahedron: Asymmetry, 2010, 21, 1135;
(h) C. You, S. Li, X. Li, J. Lan, Y. Yang, L. W. Chung, H. Lv and
X. Zhang, J. Am. Chem. Soc., 2018, 140, 4977; (i) X. Ren, Z. Zheng,
L. Zhang, Z. Wang, C. Xia and K. Ding, Angew. Chem., Int. Ed., 2017,
56, 310; ( j) Y. Yuki, K. Takahashi, Y. Tanaka and K. Nozaki, J. Am.
Chem. Soc., 2013, 135, 17393; (k) L. J. Jongkind, J. A. A. W. Elemans
and J. N. H. Reek, Angew. Chem., Int. Ed., 2019, 58, 2696.
2 (a) C. Botteghi and C. Salomon, Tetrahedron Lett., 1974, 15, 4285;
(b) H. Greenfield, J. H. Wotiz and I. Wender, J. Org. Chem., 1957,
22, 542; (c) K. Doyama, T. Joh, T. Shiohara and S. Takahashi, Bull.
Chem. Soc. Jpn., 1988, 61, 4353; (d) E. M. Campi, W. R. Jackson and
Y. Nilsson, Tetrahedron Lett., 1991, 32, 1093; (e) P. Nombel, N. Lugan,
F. Mulla and G. Lavigne, Organometallics, 1994, 13, 4673; ( f ) X. Ren,
L. Zhang, Z. Wang, C. Xia and K. Ding, J. Mol. Catal., 2016, 30, 497;
(g) W. Fang and B. Breit, Angew. Chem., Int. Ed., 2018, 56, 14817.
3 D. Rowe, Perfum. Flavor., 2000, 25, 1.
4 J. R. Johnson, G. D. Cuny and S. L. Buchwald, Angew. Chem., Int. Ed.
Engl., 1995, 34, 1760.
5 Y. Ishii, K. Miyashita, K. Kamita and M. Hidai, J. Am. Chem. Soc.,
1997, 119, 6448.
6 (a) B. G. Van den Hoven and H. Alper, J. Org. Chem., 1999, 64, 3964;
(b) B. G. Van den Hoven and H. Alper, J. Org. Chem., 1999, 64, 9640.
7 V. Agabekov, W. Seiche and B. Breit, Chem. Sci., 2013, 4, 2418.
8 X. Fang, M. Zhang, R. Jackstell and M. Beller, Angew. Chem., Int. Ed.,
2013, 52, 4645.
9 Z. Zhang, Q. Wang, C. Chen, Z. Han, X. Dong and X. Zhang, Org.
Lett., 2016, 18, 3290.
10 G. Tan, Y. Wu, Y. Shi and J. You, Angew. Chem., Int. Ed., 2019, 58, 7440.
11 (a) Z. B. Shifrina, V. G. Matveeva and L. M. Bronstein, Chem. Rev., 2019,
DOI: 10.1021/acs.chemrev.9b00137; (b) S. Kramer, N. R. Bennedsen and
S. Kegnæs, ACS Catal., 2018, 8, 6961; (c) Q. Sun, Z. Dai, X. Meng and
F.-S. Xiao, Chem. Soc. Rev., 2015, 44, 6018; (d) P. Kaur, J. T. Hupp and
S. B. T. Nguyen, ACS Catal., 2011, 1, 819.
12 (a) C. Li, W. Wang, L. Yan and Y. Ding, Front. Chem. Sci. Eng., 2018,
12, 113; (b) Q. Sun, B. Aguila, G. Verma, X. Liu, Z. Dai, F. Deng,
X. Meng, F.-S. Xiao and S. Ma, Chem, 2016, 1, 628; (c) Y. Wang,
L. Yan, C. Li, M. Jiang, Z. Zhao, G. Hou and Y. Ding, J. Catal., 2018,
368, 197; (d) C. Li, K. Sun, W. Wang, L. Yan, X. Sun, Y. Wang,
K. Xiong, Z. Zhan, Z. Jiang and Y. Ding, J. Catal., 2017, 353, 123;
(e) Y. Tang, K. Dong, S. Wang, Q. Sun, X. Meng and F.-S. Xiao, Mol.
Catal., 2019, 474, 110408.
Fig. 3 Recycling studies of the Rh/POL-BINAPa&PPh3 in diphenylacetylene
hydroformylation. Reaction conditions: 28.0 mg Rh/POL-BINAPa&PPh3,
diphenylacetylene (0.95 g), S/C = 1000, CO/H2 = 5/5 bar, toluene (7.0 mL),
70 1C for 8 h.
catalyst, the residual liquid showed no activity in the hydro-
formylation of diphenylacetylene. The Rh species in the filtrate
after each run were undetectable (o0.1 ppm) by ICP-MS
analysis, indicating the strong coordination ability of the poly-
mer with Rh species. The recovered catalyst was characterized
by XPS and FT-IR (Fig. S9, S11 and S14, ESI†), which exhibited
similar results to the original catalyst. Additionally, the N2
sorption isotherm showed decreased surface area and pore
volume (Fig. S5, ESI†).
In summary, a new porous organic polymer (POL-BINAPa&
PPh3) was synthesized through copolymerization of the vinyl-
functionalized phosphoramidite and triphenylphosphane
ligands. After supporting with Rh species, the obtained hetero-
geneous catalyst (Rh/POL-BINAPa&PPh3) showed good performance
in the hydroformylation of various symmetrical and unsymmetrical
alkynes to afford the corresponding a,b-unsaturated aldehyde
products with high selectivity, activity and recyclability. Remark-
ably, the Rh/POL-BINAPa&PPh3 heterogeneous catalyst exhibited
more catalytic activity than the comparable homogeneous
Rh/BINAPa/PPh3 system.
We are grateful for the financial support from the National
Natural Science Foundation of China (No. 21703116 and
51702180) and the Natural Science Foundation of Shandong
Province (No. ZR2016BQ24, ZR2017MB029).
13 (a) 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; (b) Q. Sun, Z. Dai, X. Meng and F.-S. Xiao, Catal. Today,
2017, 298, 40.
14 Q. Sun, Z. Dai, X. Liu, N. Sheng, F. Deng, X. Meng and F.-S. Xiao,
J. Am. Chem. Soc., 2015, 137, 5204.
Conflicts of interest
15 (a) C. Li, K. Xiong, L. Yan, M. Jiang, X. Song, T. Wang, X. Chen,
Z. Zhan and Y. Ding, Catal. Sci. Technol., 2016, 6, 2143; (b) C. Li,
L. Yan, L. Lu, K. Xiong, W. Wang, M. Jiang, J. Liu, X. Song, Z. Zhan,
Z. Jiang and Y. Ding, Green Chem., 2016, 18, 2995; (c) Y. Wang, L. Yan,
C. Li, M. Jiang, W. Wang and Y. Ding, Appl. Catal., A, 2018, 551, 98.
The authors declare no conflict of interest.
References
1 (a) C. Claver and P. W. N. M. van Leeuwen, Rhodium Catalyzed 16 X. Jia, Z. Liang, J. Chen, J. Lv, K. Zhang, M. Gao, L. Zong and C. Xie,
Hydroformylation, Kluwer Academic Publishers, Dordrecht, The Org. Lett., 2019, 21, 2147.
Netherlands, 2002; (b) R. Franke, D. Selent and A. Borner, Chem. 17 X. Jia, X. Ren, Z. Wang, C. Xia and K. Ding, Chin. J. Org. Chem., 2019,
Rev., 2012, 112, 5675; (c) J. Pospech, I. Fleischer, R. Franke, 39, 207.
S. Buchholz and M. Beller, Angew. Chem., Int. Ed., 2013, 52, 2852; 18 R. A. Taylor, B. P. Santora and M. R. Gagne, Org. Lett., 2000, 2, 1781.
¨
13724 | Chem. Commun., 2019, 55, 13721--13724
This journal is ©The Royal Society of Chemistry 2019