Communication
Homochiral Crystallization of Metal–Organic Silver Frameworks: Asymmetric [3+2] Cycloaddition of an Azomethine Ylide†
Xu Jing,
Dr. Cheng He,
Dapeng Dong,
Linlin Yang,
Prof. Chunying Duan,
Xu Jing
State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian, 116023 (P.R. China)
Search for more papers by this authorDr. Cheng He
State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian, 116023 (P.R. China)
Search for more papers by this authorDapeng Dong
State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian, 116023 (P.R. China)
Search for more papers by this authorLinlin Yang
State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian, 116023 (P.R. China)
Search for more papers by this authorCorresponding Author
Prof. Chunying Duan
State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian, 116023 (P.R. China)
State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian, 116023 (P.R. China)Search for more papers by this authorXu Jing,
Dr. Cheng He,
Dapeng Dong,
Linlin Yang,
Prof. Chunying Duan,
Xu Jing
State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian, 116023 (P.R. China)
Search for more papers by this authorDr. Cheng He
State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian, 116023 (P.R. China)
Search for more papers by this authorDapeng Dong
State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian, 116023 (P.R. China)
Search for more papers by this authorLinlin Yang
State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian, 116023 (P.R. China)
Search for more papers by this authorCorresponding Author
Prof. Chunying Duan
State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian, 116023 (P.R. China)
State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian, 116023 (P.R. China)Search for more papers by this author†
We gratefully acknowledge financial support from the NSFC (21171029 and 21025102).
Graphical Abstract
Enantiomeric silver-based MOFs were obtained through a homochiral crystallization of cinchonine and cinchonidine enantiomers as chiral adducts with silver. These MOFs exhibited excellent catalytic activity for asymmetric [3+2] cycloaddition (see scheme), giving products with high enantioselectivity.
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References
- 1
- 1aO. K. Farha, J. T. Hupp, Acc. Chem. Res. 2010, 43, 1166–1175;
- 1bM. D. Allendorf, C. A. Bauer, R. K. Bhakta, R. J. T. Houk, Chem. Soc. Rev. 2009, 38, 1330–1352;
- 1cY.-B. Zhang, W. X. Zhang, F. Y. Feng, J. P. Zhang, X. M. Chen, Angew. Chem. 2009, 121, 5391; Angew. Chem. Int. Ed. 2009, 48, 5287–5290;
- 1dM. Kurmoo, Chem. Soc. Rev. 2009, 38, 1353–1379;
- 1eJ. R. Li, R. J. Kuppler, H. C. Zhou, Chem. Soc. Rev. 2009, 38, 1477–1504;
- 1fD. Maspoch, D. RuizMolina, J. Veciana, Chem. Soc. Rev. 2007, 36, 770–818.
- 2
- 2aA. Corma, H. García, F. X. L. Xamena, Chem. Rev. 2010, 110, 4606–4655;
- 2bJ. Lee, O. K. Farha, J. Roberts, K. A. Scheidt, S. T. Nguyen, J. T. Hupp, Chem. Soc. Rev. 2009, 38, 1450–1459;
- 2cD. Farrusseng, S. Aguado, C. Pinel, Angew. Chem. 2009, 121, 7638–7649;
10.1002/ange.200806063 Google ScholarAngew. Chem. Int. Ed. 2009, 48, 7502–7513;
- 2dA. U. Czaja, N. Trukhan, U. Müller, Chem. Soc. Rev. 2009, 38, 1284–1293.
- 3
- 3aL. Yang, S. Kinoshita, T. Yamada, S. Kanda, H. Kitagawa, M. Tokunaga, T. Ishimoto, T. Ogura, R. Nagumo, A. Miyamoto, M. Koyama, Angew. Chem. 2010, 122, 5476–5479; Angew. Chem. Int. Ed. 2010, 49, 5348–5351;
- 3bE. Quartapelle Procopio, F. Linares, C. Montoro, V. Colombo, A. Maspero, E. Barea, J. A. R. Navarro, Angew. Chem. 2010, 122, 7466–7469;
10.1002/ange.201003314 Google ScholarAngew. Chem. Int. Ed. 2010, 49, 7308–7311;
- 3cC. Chizallet, S. Lazare, D. Bazer-Bachi, F. Bonnier, V. Lecocq, E. Soyer, A. A. Quoineaud, N. Bats, J. Am. Chem. Soc. 2010, 132, 12365–12377;
- 3dC. Wang, Z. G. Xie, K. E. deKrafft, W. B. Lin, J. Am. Chem. Soc. 2011, 133, 13445–13454.
- 4
- 4aM. Yoon, R. Srirambalaji, K. Kim, Chem. Rev. 2012, 112, 1196–1231;
- 4bG. Nickerl, A. Henschel, R. Grünker, K. Gedrich, S. Kaskel, Chem. Ing. Tech. 2011, 83, 90–103;
- 4cY. Liu, W. M. Xuan, Y. Cui, Adv. Mater. 2010, 22, 4112–4135;
- 4dL. Ma, C. Abney, W. B. Lin, Chem. Soc. Rev. 2009, 38, 1248–1256;
- 4eM. Heitbaum, F. Glorius, I. Escher, Angew. Chem. 2006, 118, 4850–4881;
10.1002/ange.200504212 Google ScholarAngew. Chem. Int. Ed. 2006, 45, 4732–4762.
- 5
- 5aL. Ma, J. M. Falkowski, C. Abney, W. B. Lin, Nat. Chem. 2010, 2, 838–846;
- 5bD. B. Dang, P. Y. Wu, C. He, Z. Xie, C. Y. Duan, J. Am. Chem. Soc. 2010, 133, 14566–14568;
- 5cT. Kawasaki, S. Kamimura, A. Amihara, K. Suzuki, K. Soai, Angew. Chem. 2011, 123, 6928–6930; Angew. Chem. Int. Ed. 2011, 50, 6796–6798.
- 6
- 6aD. J. Lun, G. I. N. Waterhouse, S. G. Telfer, J. Am. Chem. Soc. 2011, 133, 5806–5809;
- 6bM. Banerjee, S. Das, M. Yoon, H. J. Choi, M. H. Hyun, S. M. Park, G. Seo, K. Kim, J. Am. Chem. Soc. 2009, 131, 7524–7525;
- 6cF. J. Song, C. Wang, J. M. Falkowski, L. Q. Ma, W. B. Lin, J. Am. Chem. Soc. 2010, 132, 15390–15398.
- 7
- 7aM. Naodovic, H. Yamamoto, Chem. Rev. 2008, 108, 3132–3148;
- 7bA. Fürstner, Chem. Soc. Rev. 2009, 38, 3208–3221;
- 7cS. Díez-González, N. Marion, P. S. Nolan, Chem. Rev. 2009, 109, 3612–3676;
- 7dL. Hao, Z. P. Zhan, Curr. Org. Chem. 2011, 15, 1625–1643.
- 8
- 8aH. Y. Kim, H. J. Shih, W. E. Knabe, K. G. Oh, Angew. Chem. 2009, 121, 7556–7559; Angew. Chem. Int. Ed. 2009, 48, 7420–7423;
- 8bL. C. Wieland, E. M. Vieira, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc. 2009, 131, 570–576;
- 8cY. Yamashita, X. X. Guo, R. Takashita, S. Kobayashi, J. Am. Chem. Soc. 2010, 132, 3262–3263.
- 9
- 9aT. Arai, A. Mishiro, N. Yokoyama, K. Suzuki, H. Sata, J. Am. Chem. Soc. 2010, 132, 5338–5339;
- 9bX. X. Yan, Q. Peng, Y. Zhang, K. Zhang, W. Hong, X. L. Hou, Y. D. Wu, Angew. Chem. 2006, 118, 2013–2017; Angew. Chem. Int. Ed. 2006, 45, 1979–1983;
- 9cN. S. Josephsohn, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc. 2003, 125, 4018–4019.
- 10
- 10aR. P. Lemieux, Acc. Chem. Res. 2001, 34, 845–853;
- 10bJ. Crassous, Chem. Soc. Rev. 2009, 38, 830–845;
- 10cC. He, Y. G. Zhao, D. Guo, Z. H. Lin, C. Y. Duan, Eur. J. Inorg. Chem. 2007, 3451–3463.
- 11
- 11aF. Sladojevich, A. Trabocchi, A. Guarna, D. J. Dixon, J. Am. Chem. Soc. 2011, 133, 1710–1713;
- 11bC. Alemparte, G. Blay, K. A. Jørgensen, Org. Lett. 2005, 7, 4569–4572;
- 11cR. E. Morris, X. H. Bu, Nat. Chem. 2010, 2, 353–361.
- 12Crystal data for Ag-TPHA-1: C97H117N26O7Ag3B3F12Cl3, M=2449.56, cubic, space group I213, yellow block, a=25.381(4) Å, V=16350(5) Å3, Z=4, ρcalcd=0.993 g cm−3, μ(Mo-Kα)=0.462 mm−1, T=180(2) K. 4772 unique reflections [Rint=0.1304]. Final R1 [with I>2σ(I)]=0.0777, wR2 (all data)=0.1844. Crystal data for Ag-TPHA-2: C97H117N26O7Ag3B3F12Cl3, M=2449.56, cubic, space group I213, yellow block, a=25.369(5) Å, V=16328(6) Å3, Z=4, ρcalcd=0.994 g cm−3, μ(Mo-Kα)=0.462 mm−1, T=180(2) K. 4796 unique reflections [Rint=0.1355]. Final R1 [with I>2σ(I)]=0.0726, wR2 (all data)=0.1744.
- 13
- 13aA. F. Wells, 3D Nets and Polyhedra, Wiley-Interscience, New York, 1977;
- 13bG. Pringle, Acta Crystallogr. Sect. B 1972, 28, 2326;
- 13cS. R. Batten, R. Robson, Angew. Chem. 1998, 110, 1558–1595;
10.1002/(SICI)1521-3757(19980605)110:11<1558::AID-ANGE1558>3.0.CO;2-7 Google ScholarAngew. Chem. Int. Ed. 1998, 37, 1460–1494.10.1002/(SICI)1521-3773(19980619)37:11<1460::AID-ANIE1460>3.0.CO;2-Z CAS PubMed Web of Science® Google Scholar
- 14
- 14aQ. Z. Sun, Y. Bai, G. J. He, C. Y. Duan, Z. H. Lin, Q. J. Meng, Chem. Commun. 2006, 2777–2779;
- 14bY. Bai, C. Y. Duan, P. Cai, D. B. Dang, Q. J. Meng, Dalton Trans. 2005, 2678–2680.
- 15
- 15aD. K. Kondepudi, J. Laudadio, K. Asakura, J. Am. Chem. Soc. 1999, 121, 1448–1451;
- 15bD. K. Kondepudi, R. J. Kaufman, N. Singh, Science 1990, 250, 975–977.
- 16
- 16aL. Perez-Gatcia, D. B. Amabilino, Chem. Soc. Rev. 2007, 36, 941–952;
- 16bD. Guo, K. L. Pang, C. Y. Duan, Y. G. Zhao, Q. J. Meng, Chem. Lett. 2002, 10, 1014–1015.
- 17Crystal data for Ag-1: C97H117N26O7Ag3B3F12Cl3, M=2449.56, Cubic, space group I213, yellow block, a=25.689(1) Å, V=16952(1) Å3, Z=4, ρcald=0.958 g cm−3, μ(Mo-Kα)=0.445 mm−1, T=180(2) K. 4945 unique reflections [Rint=0.1327]. Final R1 [with I>2σ(I)]=0.0710, wR2 (all data)=0.1851. Crystal data for Ag-2: C97H117N26O7Ag3B3F12Cl3, M=2449.56, Cubic, space group I213, yellow block, a=25.574(3) Å, V=16726(3) Å3, Z=4, ρcald=0.971 g cm−3, μ(Mo-Kα)=0.451 mm−1, T=180(2) K. 4758 unique reflections [Rint=0.0947]. Final R1 [with I>2σ(I)]=0.0783, wR2 (all data)=0.1459.
- 18
- 18aD. B. Dang, P. Y. Wu, C. He, Z. Xie, C. Y. Duan, J. Am. Chem. Soc. 2010, 132, 14321–14323;
- 18bJ. Zhang, S. M. Chen, T. Wu, P. Y. Feng, X. H. Bu, J. Am. Chem. Soc. 2008, 130, 12882–12883.
- 19
- 19aJ. M. Longmire, B. Wang, X. M. Zhang, J. Am. Chem. Soc. 2002, 124, 13400–13401;
- 19bC. Nájera, M. D. Retamosa, J. M. Sansano, Org. Lett. 2007, 9, 4025–4028.
- 20Crystal data for Ag-3: C103H116N22O11Ag3B3F12Cl6, M=2634.92, Cubic, space group I213, yellow block, a=25.582(1) Å, V=16743(1) Å3, Z=4, ρcald=1.045 cm−3, μ(Mo-Kα)=0.502 mm−1, T=180(2) K. 4790 unique reflections [Rint=0.0809]. Final R1 [with I>2σ(I)]=0.0866, wR2 (all data)=0.2044.
- 21Q. A. Chen, D. S. Wang, Y. G. Zhou, Chem. Commun. 2010, 46, 4043–4051.
- 22The two dimensional sizes of the molecules of MBA and the product are calculated as 3.7×2.8 and 4.8×5.2 Å2, respectively, possibly allowing the ingress or egress of the molecules of the substrates and the product through the cross section (7.5×8.0 Å2) of the channels within the silver(I) containing MOFs.
- 23
- 23aS. Horike, M. Dinca, K. Tamaki, J. R. Long, J. Am. Chem. Soc. 2008, 130, 5854–5855;
- 23bS. Hasegawa, S. Horike, R. Matsuda, S. Furukawa, K. Mochizuki, Y. Kinoshita, S. Kitagawa, J. Am. Chem. Soc. 2007, 129, 2607–2614.
- 24CCDC 860787 (1), 860788 (2), 860785 (Ag-1), 860786 (Ag-2), and 885237 (Ag-3) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
