Citation: Leung Man Pan, Yeung Chung Chiu, Choy Pui Ying, So Chau Ming, Kwong Fuk Yee. Facile One-Pot Assembly of New 5-Substituted P, O-Type Indolylphosphine Ligands for Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling of Aryl Chlorides[J]. Chinese Journal of Organic Chemistry, ;2020, 40(10): 3338-3346. doi: 10.6023/cjoc202005069 shu

Facile One-Pot Assembly of New 5-Substituted P, O-Type Indolylphosphine Ligands for Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling of Aryl Chlorides

a.
Department of Chemistry, The Chinese University of Hong Kong, Hong Kong
b.
Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hong Kong

Corresponding author: Kwong Fuk Yee, fykwong@cuhk.edu.hk
Received Date: 26 May 2020
Revised Date: 3 July 2020
Available Online: 15 July 2020
Fund Project: the General Research Fund (GRF) from Research Grants Council of Hong Kong (RGC) 14304519Project supported by the Guangdong Basic and Applied Basic Research Foundation (No. 2019A1515011357), and the General Research Fund (GRF) from Research Grants Council of Hong Kong (RGC) (No. 14304519)the Guangdong Basic and Applied Basic Research Foundation 2019A1515011357

Figures(3)

A series of P, O-type indolylphosphine ligands with different substituted variants have been synthesized by a simple one-pot protocol from readily available and inexpensive materials. These ligands show "substituent effect" with respected to the efficacy in promoting palladium-catalyzed Suzuki-Miyaura cross-coupling of aryl chlorides. This new Pd/L1 catalyst system particularly allows the catalyst loading reaching the level of 0.01 mol% Pd.
- palladium,
- ligand design,
- cross-coupling,
- phosphine,
- P, O-ligand
1. [1]
  For selected books, see:
  (a) Negishi, E. Handbook of Organopalladium Chemistry for Organic Synthesis, Vols. 1~2, Wiley-Interscience, New York, 2002.
  (b) de Meijere, A.; Diederich, F. Metal-Catalyzed Cross-Coupling Reactions, Vols. 1~2, Wiley-VCH, Weinheim, 2004.
  (c) Ackermann, L. Modern Arylation Methods, Wiley-VCH, Weinheim, 2009. For selected reviews, see:
  (d) Corbet, J.-P.; Mignani, G. Chem. Rev. 2006, 106, 2651.
  (e) Johansson Seechurn, C. C. C.; Kitching, M. O.; Colacot, T. J.; Snieckus, V. Angew. Chem., Int. Ed. 2012, 51, 5062.
  (f) Biffis, A.; Centomo, P.; Del Zotto, A.; Zecca, M. Chem. Rev. 2018, 118, 2249.
  (g) Zhang, Y.-F.; Shi, Z.-J. Acc. Chem. Res. 2019, 52, 161.
2. [2]
  (a) Magano, J.; Dunetz, J. R. Chem. Rev. 2011, 111, 2177.
  (b) Biteau, N.; Hervin, V.; Roy, V.; Agrofoglio, L. A. In Palladium-Catalyzed Modification of Nucleosides, Nucleotides and Oligonucleotides, Vol. 1, Eds.: Kapdi, A. R.; Maiti, D.; Sanghvi, Y. S., Elsevier, Amsterdam, Netherlands, 2018, p. 37.
  (c) Devendar, P.; Qu, R.-Y.; Kang, W.-M.; He, B.; Yang, G.-F. J. Agric. Food Chem. 2018, 66, 8914.
3. [3]
  For selected book, see:
  (a) Stradiotto, M.; Lundgren, R. J. Ligand Design in Metal Chemistry, John Wiley & Sons, Hoboken, NJ, 2016. For selected articles, see:
  (b) Valente, C.; Calimsiz, S.; Hoi, K. H.; Mallik, D.; Sayah, M.; Organ, M. G. Angew. Chem., Int. Ed. 2012, 51, 3314.
  (c) Izquierdo, F.; Manzini, S.; Nolan, S. P. Chem. Commun. 2014, 50, 14926.
  (d) Wong, S. M.; Yuen, O. Y.; Choy, P. Y.; Kwong, F. Y. Coord. Chem. Rev. 2015, 293-294, 158.
  (e) Li, C.; Chen, D.; Tang, W. Synlett 2016, 2183.
4. [4]
  Fu, G. C. Acc. Chem. Res. 2008, 41, 1555. doi: 10.1021/ar800148f
5. [5]
  Hartwig, J. F. Synlett 1997, 329.
6. [6]
  (a) Surry, D. S.; Buchwald, S. L. Angew. Chem., Int. Ed. 2008, 47, 6338.
  (b) Martin, R.; Buchwald, S. L. Acc. Chem. Res. 2008, 41, 1461.
7. [7]
  Ackermann, L.; Potukuchi, H. K.; Althammer, A.; Born, R.; Mayer, P. Org. Lett. 2010, 12, 1004. doi: 10.1021/ol1000186
8. [8]
  Zapf, A.; Beller, M. Chem. Commun. 2005, 431.
9. [9]
  (a) So, C. M.; Lau, C. P.; Kwong, F. Y. Angew. Chem., Int. Ed. 2008, 47, 8059.
  (b) So, C. M.; Chow, W. K.; Choy, P. Y.; Lau, C. P.; Kwong, F. Y. Chem.-Eur. J. 2010, 16, 7996.
10. [10]
  Lundgren, R. J.; Hesp, K. D.; Stradiotto, M. Synlett 2011, 2443.
11. [11]
  (a) Tang, W.; Capacci, A. G.; Wei, X.; Li, W.; White, A.; Patel, N. D.; Savoie, J.; Gao, J. J.; Rodriguez, S.; Qu, B.; Haddad, N.; Lu, B. Z.; Krishnamurthy, D.; Yee, N. K.; Senanayake, C. H. Angew. Chem., Int. Ed. 2010, 49, 5879.
  (b) Zhao, Q.; Li, C.; Senanayake, C. H.; Tang, W. Chem.-Eur. J. 2013, 19, 2261.
12. [12]
  Liu, D.; Gao, W.; Dai, Q.; Zhang, X. Org. Lett. 2005, 7, 4907. doi: 10.1021/ol051844w
13. [13]
  Li, P.; Lu, B.; Fu, C.; Ma, S. Adv. Synth. Catal. 2013, 355, 1255. doi: 10.1002/adsc.201300207
14. [14]
  Handa, S.; Andersson, M. P.; Gallou, F.; Reilly, J.; Lipshutz, B. H. Angew. Chem., Int. Ed. 2016, 55, 4914. doi: 10.1002/anie.201510570
15. [15]
  (a) Bhilare, S.; Gayakhe, V.; Ardhapure, A. V.; Sanghavi, Y. S.; Schulzke, C.; Borozdina, Y.; Kapdi, A. R. RSC Adv. 2016, 6, 83820.
  (b) Girase, T. R.; Kapdi, A. R. Chem. Asian J. 2019, 14, 2611.
16. [16]
  For Hiesro and Doucet's selected reference, see:
  (a) Hierso, J.-C.; Fihri, A.; Amardeil, R.; Meunier, P.; Doucet, H.; Santelli, M.; Donnadieu, B. Organometallics 2003, 22, 4490. For Hoshi and Hagiwara's selected reference, see:
  (b) Hoshi, T.; Nakazawa, T.; Saitoh, I.; Mori, A.; Suzuki, T.; Sakai, J.-I.; Hagiwara, H. Org. Lett. 2008, 10, 2063. For Yu and Liu's selected reference, see:
  (c) Mao, S.-L.; Sun, Y.; Yu, G.-A.; Zhao, C.; Han, Z.-J.; Yuan, J.; Zhu, X.; Yang, Q.; Liu, S.-H. Org. Biomol. Chem. 2012, 10, 9410. For Doherty's selected reference, see:
  (d) Doherty, S.; Smyth, C. H.; Knight, J. G.; Hashmi, S. A. K. Nat. Protocols 2012, 7, 1870. For Fossey's selected reference, see:
  (e) Zhao, Y.; van Nguyen, H.; Male, L.; Craven, P.; Buckley, B. R.; Fossey, J. S. Organometallics 2018, 37, 4224.
17. [17]
  Wong, S. M.; So, C. M.; Chung, K. H.; Lau, C. P.; Kwong, F. Y. Eur. J. Org. Chem. 2012, 4172.
18. [18]
  For selected references, see:
  (a) Wang, Z.; Guo, W. In Homogeneous Catalysis for Unreactive Bond Activation, Ed.: Shi, Z., John Wiley & Sons, Hoboken, NJ, 2015, p. 1.
  (b) Braunstein, P.; Naud, F. Angew. Chem., Int. Ed. 2001, 40, 680.
  (c) Weng, Z.; Teo, S.; Hor, T. S. A. Acc. Chem. Res. 2007, 40, 676.
  (d) Zhang, W.-H.; Chien, S. W.; Hor, T. S. A. Coord. Chem. Rev. 2011, 255, 1991.
  (e) Guram, A. S. Org. Process Res. Dev. 2016, 20, 1754.
19. [19]
  Kwong, F. Y.; Chan, A. S. C. Synlett 2008, 1440.
20. [20]
  (a) Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722.
  (b) Amatore, C.; Fuxa, A.; Jutand, A. Chem.-Eur. J. 2000, 6, 1474.
21. [21]
  (a) Bei, X.; Crevier, T.; Guram, A. S.; Jandeleit, B.; Powers, T. S.; Turner, H. W.; Uno, T.; Weinberg, W. H. Tetrahedron Lett. 1999, 40, 3855.
  (b) Bei, X.; Turner, H. W.; Weinberg, W. H.; Guram, A. S.; Petersen, J. L. J. Org. Chem. 1999, 64, 6797.
22. [22]
  Teo, S.; Weng, Z.; Hor, T. S. A. Organometallics 2006, 25, 1199. doi: 10.1021/om050791j
23. [23]
  (a) Kwong, F. Y.; Lam, W. H.; Yeung, C. H.; Chan, K. S.; Chan, A. S. C. Chem. Commun. 2004, 1922.
  (b) Chen, G.; Lam, W. H.; Fok, W. S.; Lee, H. W.; Kwong, F. Y. Chem. Asian J. 2007, 2, 306.
  (c) So, C. M.; Yeung, C. C.; Lau, C. P.; Kwong, F. Y. J. Org. Chem. 2008, 73, 7803.
24. [24]
  (a) Dai, W.-M.; Li, Y.; Zhang, Y.; Lai, K. W.; Wu, J. Tetrahedron Lett. 2004, 45, 1999.
  (b) Dai, W.-M.; Zhang, Y. Tetrahedron Lett. 2005, 46, 1377.
  (c) Dai, W.-M.; Li, Y.; Zhang, Y.; Yue, C.; Wu, J. Chem.-Eur. J. 2008, 14, 5538.
25. [25]
  Ullah, E.; McNulty, J.; Robertson, A. Tetrahedron Lett. 2009, 50, 5599. doi: 10.1016/j.tetlet.2009.07.088
26. [26]
  (a) Schaarschmidt, D.; Lang, H. Eur. J. Inorg. Chem. 2010, 4811.
  (b) Schaarschmidt, D.; Lang, H. ACS Catal. 2011, 1, 411.
27. [27]
  (a) Chow, W. K.; So, C. M.; Lau, C. P.; Kwong, F. Y. J. Org. Chem. 2010, 75, 5109.
  (b) Wong, P. Y.; Chow, W. K.; Chung, K. H.; So, C. M.; Lau, C. P.; Kwong, F. Y. Chem. Commun. 2011, 47, 8328.
  (c) To, S. C.; Kwong, F. Y. Chem. Commun. 2011, 47, 5079.
  (d) Chow, W. K.; Yuen, O. Y.; So, C. M.; Wong, W. T.; Kwong, F. Y. J. Org. Chem. 2012, 77, 3543.
  (e) Leung, M. P.; Choy, P. Y.; Lai, W. I.; Gan, K. B.; Kwong, F. Y. Org. Process Res. Dev. 2019, 23, 1602.
28. [28]
  Armarego, W. L. F. Purification of Laboratory Chemicals, Butterworth-Heinemann, Oxford, UK, 2017.
29. [29]
  Choy, P. Y.; Yuen, O. Y.; Leung, M. P.; Chow, W. K.; Kwong, F. Y. Eur. J. Org. Chem. 2020, 2846.
30. [30]
  Lee, H. W.; Lam, F. L.; So, C. M.; Lau, C. P.; Chan, A. S. C.; Kwong, F. Y. Angew. Chem., Int. Ed. 2009, 48, 7436. doi: 10.1002/anie.200904033
31. [31]
  Wu, Y.; Choy, P. Y.; Kwong, F. Y. Org. Biomol. Chem. 2014, 12, 6820. doi: 10.1039/C4OB01211A
32. [32]
  Chung, K. H.; So, C. M.; Wong, S. M.; Luk, C. H.; Zhou, Z.; Lau, C. P.; Kwong, F. Y. Chem. Commun. 2012, 48, 1967. doi: 10.1039/c2cc15972d
33. [33]
  McNulty, J.; Capretta, A.; Wilson, J.; Dyck, J.; Adjabeng, G.; Robertson, A. Chem. Commun. 2002, 1986.
34. [34]
  So, C. M.; Lau, C. P.; Kwong, F. Y. Org. Lett. 2007, 9, 2795. doi: 10.1021/ol070898y
35. [35]
  Mingji, D.; Liang, B.; Wang, C.; You, Z.; Xiang, J.; Dong, G.; Chen, J.; Yang, Z. Adv. Synth. Catal. 2004, 346, 1669. doi: 10.1002/adsc.200404165
36. [36]
  Zhang, J.; Zhao, L.; Song, M.; Mak, T. C. W.; Wu, Y. J. Organomet. Chem. 2006, 691, 1301. doi: 10.1016/j.jorganchem.2005.11.027
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