Communication
ChemComm
2015, 21, 12079; (i) P. Puthiaraj and K. Pitchumani, Green Chem.,
2014, 16, 4223; ( j) X. Xu, Y. Li, Y. T. Gong, P. F. Zhang, H. R. Li and
Y. Wang, J. Am. Chem. Soc., 2012, 134, 16987.
halide species reacts directly with a nucleophile (amine) and
the base to form the amide (mono carbonylation product).
We speculate that lower temperatures are favourable for absorbing
more CO in the pore canals, and the increased concentration of
CO is prone to coordinate to the Pd species.3c,16 Such speculations
are proved by our experimental results.
5 (a) J. Y. Lee, O. K. Farha, J. Roberts, K. A. Scheidt, S. T. Nguyen and
J. T. Hupp, Chem. Soc. Rev., 2009, 38, 1450; (b) L. Ma, C. Abney and
W. Lin, Chem. Soc. Rev., 2009, 38, 1248; (c) A. Phan, C. J. Doonan,
F. J. Uribe-romo, C. B. Knobler, M. O’keeffe and O. M. Yaghi, Acc.
Chem. Res., 2010, 43, 58; (d) K.-B. Zhou and Y.-D. Li, Angew. Chem., Int.
Ed., 2012, 51, 602; (e) Z.-C. Zhang, Y.-F. Chen, S. He, J.-C. Zhang, X.-B.
Xu, Y. Yang, F. Nosheen, F. Saleem, W. He and X. Wang, Angew. Chem.,
2014, 126, 12725; ( f ) T. T. Dang, Y. Zhu, J. S. Y. Ngiam, S. C. Ghosh,
A. Chen and A. M. Seayad, ACS Catal., 2013, 3, 1406; (g) T. T. Dang,
Y. H. Zhu, J. S. Y. Ngiam, S. C. Ghosh, A. Q. Chen and A. M. Seayad,
ACS Catal., 2013, 3, 1406; (h) X. Y. Li, Y. C. Wu, L. F. Hang, D. D. Men,
W. P. Cai and Y. Li, J. Mater. Chem. C, 2015, 3, 51; (i) L. F. Hang,
C. C. Li, T. Zhang, X. Y. Li, Y. C. Wu, D. D. Wen, G. Q. Liu and Y. Li,
RSC Adv., 2014, 4, 64668; ( j) H. L. Liu, Y. L. Liu, Y. W. Li, Z. Y. Tang
and H. F. Jiang, J. Phys. Chem. C, 2010, 114, 13362.
6 (a) R.-G. Yuan, H. Ren, H.-M. He, L.-C. Jiang and G.-S. Zhu, Sci.
China Mater., 2015, 58, 38; (b) T. Y. Ma and S. Z. Qiao, ACS Catal.,
2014, 4, 3847; (c) Z.-R. Jiang, H. W. Wang, Y. L. Hu, J. L. Lu and
H.-L. Jiang, ChemSusChem, 2015, 8, 878; (d) R. Gomes, P. Bhanja and
A. Bhaumik, Chem. Commun., 2015, 51, 10050; (e) L. C. He, Y. Liu,
J. Z. Liu, Y. S. Xiong, J. Z. Zheng, Y. L. Liu and Z. Y. Tang, Angew.
Chem., Int. Ed., 2013, 52, 3741.
7 (a) S. Bhunia, R. A. Molla, V. Kumari, S. M. Islam and A. Bhaumik,
Chem. Commun., 2015, 51, 15732; (b) J. Q. Wang, J. G. W. Yang,
G. S. Yi and Y. G. Zhang, Chem. Commun., 2015, 51, 15708;
(c) Z. Z. Yang, H. Y. Zhang, B. Yu, Y. F. Zhao, Z. S. Ma, G. P. Ji,
B. X. Han and Z. M. Liu, Chem. Commun., 2015, 51, 11576;
(d) S. N. Talapaneni, O. Buyukcakir, S. H. Je, S. Srinivason, Y. Seo,
Y. Polychronopoulou and A. Coskun, Chem. Mater., 2015, 27, 6818;
(e) Q. Sun, Z. F. Dai, X. J. Meng, L. Wang and F.-S. Xiao, ACS Catal.,
2015, 5, 4556; ( f ) A. B. Chen, Y. Z. Zhang, J. Z. Chen, L. M. Chen and
Y. F. Yu, J. Mater. Chem. A, 2015, 3, 9807; (g) V. M. Suresh,
S. Bonakala, H. S. Atreya, S. Balasubramanian and T. K. Maji, ACS
Appl. Mater. Interfaces, 2014, 6, 44630; (h) Y. T. Gong, P. F. Zhang,
X. Xu, Y. Li, H. R. Li and Y. Wang, J. Catal., 2013, 297, 272.
8 L.-Y. Li, H.-X. Zhao and R.-H. Wang, ACS Catal., 2015, 5, 948.
9 X.-H. Liu, J.-G. Ma, Z. Niu, G.-M. Yang and P. Cheng, Angew. Chem.,
2015, 127, 1002.
In summary, we have reported a facile preparation of the
hybrid Pd/CTFs catalyst using the impregnation-reduction
method. This is the first example that porous material simulta-
neously captures and converts CO for one-step selective double
carbonylations of Ar–I with amines under atmospheric pressure
of CO without the assistance of any ligands. The synergetic effect
of palladium nanoparticles (catalytic center) and high porosity of
CTFs (gas adsorption) led to the accomplishment of this reaction
at atmospheric pressure instead of high pressure. Wide substrate
scopes, promising yields and selectivities, and low loading and
good recyclability of the catalysts demonstrate the effectiveness of
Pd/CTFs. Therefore, this work will be of help in the design of a
highly active and stable catalyst for gas insertion reactions via
such synergistic effects of gas capture substrates and active
catalysts.
This research was financially supported by the National
Natural Science Foundation of China (No. 21422104).
Notes and references
1 (a) A. Schoenberg, I. Bartoletti and B. F. Heck, J. Org. Chem., 1974,
39, 3318; (b) Y. Uozumi, T. Arii and T. Watanabe, J. Org. Chem., 2001,
66, 5272; (c) X.-F. Wu, P. Anbarasan, H. Neumann and M. Beller,
Angew. Chem., Int. Ed., 2010, 49, 7316; (d) F. M. Miloserdov and
V. V. Grushin, Angew. Chem., Int. Ed., 2012, 51, 3668;
(e) A. Brennfuhrer, H. Neumann and M. Beller, Angew. Chem., Int.
Ed., 2009, 48, 4114; ( f ) G. Y. Zhang, B. Gao and H.-M. Huang, Angew.
Chem., Int. Ed., 2015, 54, 7657; (g) S. T. Gadge and B. M. Bhanage,
RSC Adv., 2014, 4, 10367.
10 (a) C. E. Chan-Thaw, A. Villa, P. Katekomol, D.-S. Su, A. Thomas and
L. Prati, Nano Lett., 2010, 10, 537; (b) S. J. Ren, M. J. Bojdys,
R. Dawson, A. Laybourn, Y. Z. Khimyak, D. J. Adams and
A. I. Cooper, Adv. Mater., 2012, 24, 2357; (c) Y. Zhou, Z.-H. Xiong,
D.-P. Cao and C.-J. Liu, Chem. Commun., 2013, 49, 5633.
11 S. Gao, N. Zhao, M. Shu and S. Che, Appl. Catal., A, 2010, 388, 196.
12 X. M. Chen, G. H. Wu, J. M. Chen, X. Chen, Z. X. Xie and X. R. Wang,
J. Am. Chem. Soc., 2011, 133, 3693.
2 (a) Q. Xing, L.-J. Shi, R. Lang, C.-G. Xia and F.-W. Li, Chem. Commun.,
2012, 48, 11023; (b) N. Saito, T. Taniguchi, N. Hoshiya, S. Shuto,
M. Arisawa and Y. Sato, Green Chem., 2015, 17, 2358.
3 (a) M. Iizuka and Y. Kondo, Chem. Commun., 2006, 1739;
(b) M. Genelot, N. Villandier, A. Bendjeriou, P. Jaithong,
L. Djakovitch and V. Dufaud, Catal. Sci. Technol., 2012, 2, 1886;
(c) S.-Z. Zheng, Y. Wang, C.-Y. Zhang, J.-H. Liu and C.-G. Xia, Appl.
Organomet. Chem., 2014, 28, 48; (d) V. de la Fuente, C. Godard,
E. Zangrando, C. Claver and S. Castillon, Chem. Commun., 2012,
48, 1695; (e) H.-Y. Du, Q. Ruan, M.-H. Qi and W. Han, J. Org. Chem.,
2015, 80, 7816.
4 (a) X. Feng, X. S. Ding and D. L. Jiang, Chem. Soc. Rev., 2012,
41, 6010; (b) S.-Y. Wang, Chem. Soc. Rev., 2013, 42, 548; (c) S.-Y.
Ding and W. Wang, Chem. Soc. Rev., 2013, 42, 548; (d) L.-Y. Li,
H.-X. Zhao, J.-Y. Wang and R.-H. Wang, ACS Nano, 2014, 8, 5352;
(e) W.-Y. Gao, L. Wojtas and S. Ma, Chem. Commun., 2014, 50, 5316;
( f ) P. Kuhn, M. Antoninetti and A. Thomas, Angew. Chem., Int. Ed.,
2008, 47, 3450; (g) X. Wang, Sci. China Mater., 2015, 58, 347; (h) Z. Li,
Y. Zhi, X. Feng, X. Ding, Y. Zou, X. Liu and Y. Ma, Chem. – Eur. J.,
13 T. T. Dang, Y. H. Zhu, S. C. Ghosh, A. Q. Chen, C. L. L. Chai and
A. M. Seayad, Chem. Commun., 2012, 48, 1805.
14 J. Liu, S. Zheng, W. Sun and C. Xia, Chin. J. Chem., 2009, 27, 623.
´
´
15 (a) V. M. Fernandez-Alvarez, V. D. L. Fuente, C. Godard, S. Castillon,
´
C. Claver, F. Maseras and J. J. Carbo, Chem. – Eur. J., 2014, 20, 10982;
(b) R. A. Molla, Md. Asif lqubal, K. Ghosh, A. S. Roy, Kamaluddin
and S. M. lslam, RSC Adv., 2014, 4, 48177; (c) C.-G. Dong and Q.-S.
Hu, J. Am. Chem. Soc., 2005, 127, 10006.
16 (a) L. Wan, J. L. Wang, C. Feng, Y. H. Sun and K. X. Li, Nanoscale,
2015, 7, 6534; (b) K. Sumida, D. L. Rogow, J. A. Mason,
T. M. McDohald, E. D. Bloch, Z. R. Herm, T.-H. Bae and
J. R. Long, Chem. Rev., 2012, 112, 724.
Chem. Commun.
This journal is ©The Royal Society of Chemistry 2016