Iron Catalyzed Oxidative Hydroarylation, Methylarylation, and Diarylation of Vinylarenes to Generate Unsymmetrical 1, 1-Diarylalkanes
- Corresponding author: Bao Hongli, hlbao@fjirsm.ac.cn
Citation:
Babu Kaki Raveendra, Chen Shaowei, Li Yajun, Bao Hongli. Iron Catalyzed Oxidative Hydroarylation, Methylarylation, and Diarylation of Vinylarenes to Generate Unsymmetrical 1, 1-Diarylalkanes[J]. Chinese Journal of Organic Chemistry,
;2017, 37(5): 1160-1164.
doi:
10.6023/cjoc201702036
(a) Weissermel, K. ; Arpe, H. J. Industrielle Organische Chemie, 5th ed. , Wiley-VCH, Weinheim, Germany, 1988, p. 167.
(b) Perego, C. ; Ingallina, P. Catal. Today 2002, 73, 3.
(c) Perego, C. ; Ingallina, P. Green Chem. 2004, 6, 274.
For selected bioactive 1, 1-diarylethanes, see:
(a) Alami, M. ; Messaoudi, S. ; Hamze, A. ; Provot, O. ; Brion, J. -D. ; Liu, J. -M. ; Bignon, J. ; Bakala, J. WO 2009/147217, 2009 [Chem. Abstr. 2009, 152, 37275].
(b) Moree, W. J. ; Li, B. -F. ; Jovic, F. ; Coon, T. ; Yu, J. ; Gross, R. S. ; Tucci, F. ; Marinkovic, D. ; Zamani-Kord, S. ; Malany, S. ; Bradbury, M. J. ; M. Hermandez, L. ; O'Brien, Z. ; Wen, J. ; Wang, H. ; Hoare, S. R. J. ; Petroski, R. E. ; Sacaan, A. ; Madan, A. ; Crowe, P. D. ; Beaton, G. J. Med. Chem. 2009, 52, 5307.
(c) Beaton, G. ; Moree, W. J. ; Jovic, F. ; Coon, T. ; Yu, J. US 2006/0014797, 2006 [Chem. Abstr. 2006, 144, 128847].
(d) Chubb, N. A. L. ; Cox, M. R. ; Dauvergne, J. S. ; Ewin, R. A. ; Lauret, C. US 0167506, 2007 [Chem. Abstr. 2007, 147, 189176].
(e) Pathak, T. P. ; Osiak, J. G. ; Vaden, R. M. ; Welm, B. E. ; Sigman, M. S. Tetrahedron 2012, 68, 5203.
(f) Messaoudi, S. ; Hamze, A. ; Provot, O. ; Treguier, B. ; Dé Losada, J. R. ; Bignon, J. ; Liu, J. -M. ; Wdzieczak-Bakala, J. ; Thoret, S. ; Dubois, J. ; Brion, J. -D. ; Alami, M. ChemMedChem 2011, 6, 488.
(g) Wang, Z. ; Ai, F. ; Wang, Z. ; Zhao, W. ; Zhu, G. ; Lin, Z. ; Sun, J. J. Am. Chem. Soc. 2015, 137, 383.
For selected bioactive other 1, 1-diarylalkanes, see:
(a) Silva, D. H. S. ; Davino, S. C. ; de Moraes Barros S. B. ; Yoshida, M. J. Nat. Prod. 1999, 62, 1475.
(b) Hills, C. J. ; Winter, S. A. ; Balfour, J. A. Drugs 1998, 55, 813.
(c) Funaoka, M. Polym. Int. 1998, 47, 277.
(d) Stelmach, J. E. ; Keith, R. ; Parmee, E. R. ; Tata, J. R. WO 2006/102067, 2006 [Chem. Abstr. 2006, 145, 377567].
(e) Kainuma, M. ; Kasuga, J. -i. ; Hosoda, S. ; Wakabayashi, K. -i. ; Tanatani, A. ; Nagasawa, K. ; Miyachi, H. ; Makishima, M. ; Hashimoto, Y. Bioorg. Med. Chem. Lett. 2006, 16, 3213.
(f) Kim, R. M. ; Parmee, E. R. ; Tan, Q. ; Yang, C. -m. ; Lins, A. R. WO 2007/136577, 2007 [Chem. Abstr. 2007, 148, 33513].
(g) Malhotra, B. ; Gandelman, K. ; Sachse, R. ; Wood, N. ; Michel, M. C. Curr. Med. Chem. 2009, 16, 4481.
(h) Hu, Q. Z. ; Yin, L. N. ; Jagusch, C. ; Hille, U. E. ; Hartmann, R. W. J. Med. Chem. 2010, 53, 5049.
(i) Babu, K. R. ; Khan, F. A. Tetrahedron Lett. 2015, 56, 4067.
(a) Botteghi, C. ; Corrias, T. ; Marchetti, M. ; Paganelli, S. ; Piccolo, O. Org. Proc. Res. Dev. 2002, 6, 379.
(b) Cheltsov, A. V. ; Aoyagi, M. ; Aleshin, A. ; Yu, E. C. -W. ; Gilliland, T. ; Zhai, D. ; Bobkov, A. A. ; Reed, J. C. ; Liddingtonand, R. C. ; Abagyan, R. J. Med. Chem. 2010, 53, 3899.
(c) Ochsner, M. ; Creba, J. ; Walker, J. ; Bentley, P. ; Muakkassah-Kelly, S. F. Biochem. Pharmacol. 1990, 40, 2247.
(d) Tscheschet, R. ; Delhvi, M. S. ; Sepúlveda-Boza, S. ; Zilliken, F. ; Kirfeland, A. ; Will, G. Liebigs Ann. Chem. 1985, 1985, 2465.
Selected recent reviews on the synthesis of 1, 1-diarylalkanes:
(a) Chen, C. ; Dong, X. -Q. ; Zhang, X. Org. Chem. Front. 2016, 3, 1359.
(b) Mondal, S. ; Panda, G. RSC Adv. 2014, 4, 28317.
Selected papers for the synthesis of 1, 1-diarylalkanes via difunctionalization of olefins:
(a) Ouyang, X. -H. ; Song, R. -J. ; Hu, M. ; Yang, Y. ; Li, J. -H. Angew. Chem., Int. Ed. 2016, 55, 3187.
(b) Tang, E. ; Zhao, Y. ; Li, W. ; Wang, W. ; Zhang, M. ; Dai, X. Org. Lett. 2016, 18, 912.
Selected papers for the synthesis of 1, 1-diarylalkanes via 1, 1-diarylalkenes hydrogenation:
(a) Chen, J. ; Chen, C. ; Ji, C. ; Lu, Z. Org. Lett. 2016, 18, 1594.
(b) Wang, X. ; Guram, A. ; Caille, S. ; Hu, J. ; Preston, J. P. ; Ronk, M. ; Walker, S. Org. Lett. 2011, 13, 1881.
(c) Yan, Q. ; Kong, D. ; Zhao, W. ; Zi, G. ; Hou, G. J. Org. Chem. 2016, 81, 2070.
Selected papers for the synthesis of 1, 1-diarylalkanes via benzylic C-H functionalization:
(a) Sha, S. -C. ; Jiang, H. ; Mao, J. ; Bellomo, A. ; Jeong, S. A. ; Walsh, P. J. Angew. Chem., Int. Ed. 2016, 56, 1070.
(b) Ronson, T. O. ; Carney, J. R. ; Whitwood, A. C. ; Taylor, R. J. K. ; Fairlamb, I. J. S. Chem. Commun. 2015, 51, 3466.
Selected papers for the synthesis of 1, 1-diarylalkanes via Friedel-Crafts reactions:
(a) Pallikonda, G. ; Chakravarty, M. J. Org. Chem. 2016, 81, 2135.
(b) Niggemann, M. ; Meel, M. J. Angew. Chem., Int. Ed. 2010, 49, 3684.
(c) Iovel, I. ; Mertins, K. ; Kischel, J. ; Zapf, A. ; Beller, M. Angew. Chem., Int. Ed. 2005, 44, 3913.
(d) Mertins, K. ; Iovel, I. ; Kischel, J. ; Zapf, A. ; Beller, M. Adv. Synth. Catal. 2006, 348, 691.
Other methods for the 1, 1-diarylalkanes synthesis:
(a) Giedyk, M. ; Goliszewska, K. ; Ó Proinsias, K. ; Gryko, D. Chem. Commun. 2016, 52, 1389.
(b) Guduguntla, S. ; Hornillos, V. ; Tessier, R. ; Fañanás-Mastral, M. ; Feringa, B. L. Org. Lett. 2016, 18, 252.
(a) Wang, M. Z. ; Wong, M. K. ; Che, C. M. Chem. Eur. J. 2008, 14, 8353.
(b) Hu, X. B. ; Martin, D. ; Melaimi, M. ; Bertrand, G. J. Am. Chem. Soc. 2014, 136, 13594.
(a) Sun, H. B. ; Li, B. ; Hua, R. M. ; Yin, Y. W. Eur. J. Org. Chem. 2006, 4231.
(b) Rueping, M. ; Nachtsheim, B. J. ; Scheidt, T. Org. Lett. 2006, 8, 3717.
Hu, F.; Patel, M.; Luo, F. X.; Flach, C.; Mendelsohn, R.; Garfunkel, E.; He, H. X.; Szostak, M. J. Am. Chem. Soc. 2015, 137, 14473.
doi: 10.1021/jacs.5b09636
Kischel, J.; Jovel, I.; Mertins, K.; Zapf, A.; Beller, M. Org. Lett. 2006, 8, 19.
doi: 10.1021/ol0523143
(a) Peregoand, C. ; Ingallina, P. Green Chem. 2004, 6, 274.
(b) Peregoand, C. ; Ingallina, P. Catal. Today 2002, 73, 3.
Niggemannand, M.; Bisek, N. Chem. Eur. J. 2010, 16, 11246.
doi: 10.1002/chem.v16:37
Perez, M.; Mahdi, T.; Hounjetand, L. J.; Stephan, D. W. Chem. Commun. 2015, 51, 11301.
doi: 10.1039/C5CC03572D
(a) Anderson, L. L. ; Arnold, J. ; Bergman, R. G. J. Am. Chem. Soc. 2005, 127, 14542.
(b) Marcsekova, K. ; Doye, S. Synthesis 2007, 145.
(a) Mohan, D. C. ; Patiland, R. D. ; Adimurthy, S. Eur. J. Org. Chem. 2012, 3520.
(b) Cejka, J. ; Wichterlova, B. Catal. Rev. Sci. Eng. 2002, 44, 375.
Wen, J. Y.; Qi, H. F.; Kong, X. J.; Chen, L. G.; Yan, X. L. Synth. Commun. 2014, 44, 1893.
doi: 10.1080/00397911.2013.876547
Friis, S. D.; Pirnot, M. T.; Buchwald, S. L. J. Am. Chem. Soc. 2016, 138, 8372.
doi: 10.1021/jacs.6b04566
Crisenza, G. E. M.; Sokolova, O. O.; Bower, J. F. Angew. Chem., Int. Ed. 2015, 54, 14866.
doi: 10.1002/anie.201506581
(a) Joslin, E. E. ; McMullin, C. L. ; Gunnoe, T. B. ; Cundari, T. R. ; Sabat, M. ; Myers, W. H. Organometallics 2012, 31, 6851.
(b) Foley, N. A. ; Lee, J. P. ; Ke, Z. F. ; Gunnoe, T. B. ; Cundari, T. R. Acc. Chem. Res. 2009, 42, 585.
(c) Lail, M. ; Arrowood, B. N. ; Gunnoe, T. B. J. Am. Chem. Soc. 2003, 125, 7506.
(a) Luedtke, A. T. ; Goldberg, K. I. Angew. Chem., Int. Ed. 2008, 47, 7694.
(b) Karshtedt, D. ; Belland, A. T. ; Tilley, T. D. Organometallics 2004, 23, 4169.
Lee, S. Y.; Villani-Gale, A.; Eichman, C. C. Org. Lett. 2016, 18, 5034.
doi: 10.1021/acs.orglett.6b02492
Ma, Y.; Zhang, D.; Yan, Z.; Wang, M.; Bian, C.; Gao, X.; Bunel, E. E.; Lei, A. Org. Lett. 2015, 17, 2174.
doi: 10.1021/acs.orglett.5b00775
Tan, F.-L.; Song, R.-J.; Hu, M.; Li, J.-H. Org. Lett. 2016, 18, 3198.
doi: 10.1021/acs.orglett.6b01419
(a) Sun, C. -L. ; Li, B. -J. ; Shi, Z. -J. Chem. Rev. 2011, 111, 1293.
(b) Bauer, I. ; Knölker, H. -J. Chem. Rev. 2015, 115, 3170.
(c) Sherry, B. D. ; Fürstner, A. Acc. Chem. Res. 2008, 41, 1500.
(d) Fürstner, A. Angew. Chem., Int. Ed. 2009, 48, 1364.
(a) Li, Y. ; Han, Y. ; Xiong, H. ; Zhu, N. ; Qian, B. ; Ye, C. ; Kantchev, E. A. ; Bao, H. Org. Lett. 2016, 18, 392.
(b) Zhu, N. ; Zhao, J. ; Bao, H. Chem. Sci. 2017, 8, 2081.
(c) Babu, K. R. ; Zhu, N. ; Bao, H. Org. Lett. 2017, 19, 46.
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