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 shu

Iron Catalyzed Oxidative Hydroarylation, Methylarylation, and Diarylation of Vinylarenes to Generate Unsymmetrical 1, 1-Diarylalkanes

a.
College of Chemistry and Chemical Engineering, Fuzhou University, Fuzhou 350108
b.
Key Laboratory of Coal to Ethylene Glycol and Its Related Technology, Fujian Institute of Research on the Structure of Matter, University of Chinese Academy of Sciences, Fuzhou 350002

Corresponding author: Bao Hongli, hlbao@fjirsm.ac.cn
Received Date: 25 February 2017
Revised Date: 25 March 2017

Fund Project: the National Natural Science Foundation of China 21672213the Strategic Priority Research Program of Chinese Academy of Sciences No.XDB20000000the National Natural Science Foundation of China 21502191the National Natural Science Foundation of China Nos.21402200the National Natural Science Foundation of China 21232001

Figures(2)

A novel iron catalyzed hydroarylation, methylarylation, and diarylation of styrenes to form unsymmetrical 1, 1-diarylalkanes with electron rich anisole and 1, 3, 5-trimethoxybenzene under mild conditions have been developed. Benzoyl peroxide is used as an oxidant for hydroarylation, whereas in the case of methylarylation and diarylation the oxidant tert-butyl peracetate is used.
- hydroarylation,
- methylarylation,
- diarylation,
- vinylarenes,
- 1, 1-diarylalkanes
1. [1]
  (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.
2. [2]
  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.
3. [3]
  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.
4. [4]
  (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.
5. [5]
  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.
6. [6]
  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.
7. [7]
  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.
8. [8]
  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.
9. [9]
  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.
10. [10]
  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.
11. [11]
  (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.
12. [12]
  (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.
13. [13]
  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
14. [14]
  Kischel, J.; Jovel, I.; Mertins, K.; Zapf, A.; Beller, M. Org. Lett. 2006, 8, 19. doi: 10.1021/ol0523143
15. [15]
  (a) Peregoand, C. ; Ingallina, P. Green Chem. 2004, 6, 274.
  (b) Peregoand, C. ; Ingallina, P. Catal. Today 2002, 73, 3.
16. [16]
  Niggemannand, M.; Bisek, N. Chem. Eur. J. 2010, 16, 11246. doi: 10.1002/chem.v16:37
17. [17]
  Perez, M.; Mahdi, T.; Hounjetand, L. J.; Stephan, D. W. Chem. Commun. 2015, 51, 11301. doi: 10.1039/C5CC03572D
18. [18]
  (a) Anderson, L. L. ; Arnold, J. ; Bergman, R. G. J. Am. Chem. Soc. 2005, 127, 14542.
  (b) Marcsekova, K. ; Doye, S. Synthesis 2007, 145.
19. [19]
  (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.
20. [20]
  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
21. [21]
  Friis, S. D.; Pirnot, M. T.; Buchwald, S. L. J. Am. Chem. Soc. 2016, 138, 8372. doi: 10.1021/jacs.6b04566
22. [22]
  Crisenza, G. E. M.; Sokolova, O. O.; Bower, J. F. Angew. Chem., Int. Ed. 2015, 54, 14866. doi: 10.1002/anie.201506581
23. [23]
  (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.
24. [24]
  (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.
25. [25]
  Lee, S. Y.; Villani-Gale, A.; Eichman, C. C. Org. Lett. 2016, 18, 5034. doi: 10.1021/acs.orglett.6b02492
26. [26]
  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
27. [27]
  Tan, F.-L.; Song, R.-J.; Hu, M.; Li, J.-H. Org. Lett. 2016, 18, 3198. doi: 10.1021/acs.orglett.6b01419
28. [28]
  (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.
29. [29]
  (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.
1. [1]
  Xiaolong Qi , Xueli Lv , Lin Gao , Jiwen Jiao , Minyan Wang , Xiaoming Wang . Dinuclear Ni enabled reductive diarylation of dienes: Intramolecular comproportionation as the key mechanistic driver. Chinese Chemical Letters, 2026, 37(9): 112189-. doi: 10.1016/j.cclet.2025.112189
2. [2]
  Wujun Jian , Mong-Feng Chiou , Yajun Li , Hongli Bao , Song Yang . Cu-catalyzed regioselective diborylation of 1,3-enynes for the efficient synthesis of 1,4-diborylated allenes. Chinese Chemical Letters, 2024, 35(5): 108980-. doi: 10.1016/j.cclet.2023.108980
3. [3]
  Chunhua Ma , Mengjiao Liu , Siyu Ouyang , Zhenwei Cui , Jingjing Bi , Yuqin Jiang , Zhiguo Zhang . Metal-free construction of diverse 1,2,4-triazolo[1,5-a]pyridines on water. Chinese Chemical Letters, 2025, 36(1): 109755-. doi: 10.1016/j.cclet.2024.109755
4. [4]
  Zijian Zhang , Fangxin Du , Lijia Liu , Yixiang Sun , Jie Xue , Hanshen Xin . 1-Azaazulene constructs: Overcoming the weak fluorescence of azulene derivatives via S₁-S₀ transitions. Chinese Chemical Letters, 2026, 37(6): 111987-. doi: 10.1016/j.cclet.2025.111987
5. [5]
  Xiao-Kang Dai , Jia-Xin Xiong , Zheng-Yan Wang , Hao-Dong Qian , Jing Zhao , Shaolin Zhou , Hao Xu . Remote copper-catalyzed asymmetric [4 + 1] annulation of yne-thienyl esters with 1,3-dicarbonyls. Chinese Chemical Letters, 2026, 37(10): 112870-. doi: 10.1016/j.cclet.2026.112870
6. [6]
  Liangfeng Yang , Liang Zeng , Yanping Zhu , Qiuan Wang , Jinheng Li . Copper-catalyzed photoredox 1,4-amidocyanation of 1,3-enynes with N-amidopyridin-1-ium salts and TMSCN: Facile access to α-amido allenyl nitriles. Chinese Chemical Letters, 2024, 35(11): 109685-. doi: 10.1016/j.cclet.2024.109685
7. [7]
  . 第41卷第1期封面和目次. Acta Physico-Chimica Sinica, 2025, 41(1): -.
8. [8]
  Huiju Cao , Lei Shi . sp¹-Hybridized linear and cyclic carbon chain. Chinese Chemical Letters, 2025, 36(4): 110466-. doi: 10.1016/j.cclet.2024.110466
9. [9]
  Huijuan Liao , Yulin Xiao , Dong Xue , Mingyu Yang , Jianyang Dong . Synthesis of 1-Benzyl Isoquinoline via the Minisci Reaction. University Chemistry, 2025, 40(7): 294-299. doi: 10.12461/PKU.DXHX202409092
10. [10]
  . Cover and Table of Contents for Vol.41 No. 12. Acta Physico-Chimica Sinica, 2026, 42(1): 0-.
11. [11]
  . . University Chemistry, 2026, 41(1): 0-0.
12. [12]
  Kangyuan Xie , Shen Chen , Zhi Ye , Min Chen , Hanying Li . Unveiling the intrinsic dielectric constant of form Ⅲ iPB-1 single crystals. Chinese Chemical Letters, 2026, 37(10): 112165-. doi: 10.1016/j.cclet.2025.112165
13. [13]
  Gaofeng WANG , Shuwen SUN , Yanfei ZHAO , Lixin MENG , Bohui WEI . Structural diversity and luminescence properties of three zinc coordination polymers based on bis(4-(1H-imidazol-1-yl)phenyl)methanone. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 849-856. doi: 10.11862/CJIC.20230479
14. [14]
  Hai-Yang Song , Jun Jiang , Yu-Hang Song , Min-Hang Zhou , Chao Wu , Xiang Chen , Wei-Min He . Supporting-electrolyte-free electrochemical [2 + 2 + 1] annulation of benzo[d]isothiazole 1,1-dioxides, N-arylglycines and paraformaldehyde. Chinese Chemical Letters, 2024, 35(6): 109246-. doi: 10.1016/j.cclet.2023.109246
15. [15]
  Zhiwei Chen , Heyun Sheng , Xue Li , Menghan Chen , Xin Li , Qiuling Song . Efficient capture of difluorocarbene by pyridinium 1,4-zwitterionic thiolates: A concise synthesis of difluoromethylene-containing 1,4-thiazine derivatives. Chinese Chemical Letters, 2024, 35(4): 108937-. doi: 10.1016/j.cclet.2023.108937
16. [16]
  Jinge Zhu , Ailing Tang , Leyi Tang , Peiqing Cong , Chao Li , Qing Guo , Zongtao Wang , Xiaoru Xu , Jiang Wu , Erjun Zhou . Chlorination of benzyl group on the terminal unit of A₂-A₁-D-A₁-A₂ type nonfullerene acceptor for high-voltage organic solar cells. Chinese Chemical Letters, 2025, 36(1): 110233-. doi: 10.1016/j.cclet.2024.110233
17. [17]
  Qi Li , Zi-Lu Wang , Yun-He Xu . Copper-catalyzed 1,4-silylcyanation of 1,3-enynes: A silyl radical-initiated approach for synthesis of difunctionalized allenes. Chinese Chemical Letters, 2025, 36(3): 109991-. doi: 10.1016/j.cclet.2024.109991
18. [18]
  Yuanyuan Ping , Wangqing Kong . 光催化碳氢键官能团化合成1-苯基-1,2-乙二醇. University Chemistry, 2025, 40(6): 238-247. doi: 10.12461/PKU.DXHX202408092
19. [19]
  Yanfen PENG , Xinyue WANG , Tianbao LIU , Xiaoshuo WU , Yujing WEI . Syntheses and luminescence of four Cd(Ⅱ)/Zn(Ⅱ) complexes constructed by 1,3‐bis(4H‐1,2,4‐triazole)benzene. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1416-1426. doi: 10.11862/CJIC.20250018
20. [20]
  Yuan Xiong , Lan-Hui Qin , Bei Zhao , Lei-Zhi Xu , Yu-Fan Fan , Tian Tian , Hai-Rong Zeng , Ting Liu , Jian Huang , Jian-Ming Sun , Zhen-Hao Tian , Guang-Bo Ge . Structure-based design and development of halogenated-naphthalimides as potent hCYP1B1 inhibitors for overcoming paclitaxel resistance. Chinese Chemical Letters, 2025, 36(11): 110812-. doi: 10.1016/j.cclet.2024.110812

Get Citation

PDF

XML

Metrics

PDF Downloads(16)
Abstract views(2811)
HTML views(310)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142