Facile One-Pot Assembly of New 5-Substituted P, O-Type Indolylphosphine Ligands for Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling of Aryl Chlorides
- Corresponding author: Kwong Fuk Yee, fykwong@cuhk.edu.hk
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
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.
(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.
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.
Fu, G. C. Acc. Chem. Res. 2008, 41, 1555.
doi: 10.1021/ar800148f
Hartwig, J. F. Synlett 1997, 329.
(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.
Ackermann, L.; Potukuchi, H. K.; Althammer, A.; Born, R.; Mayer, P. Org. Lett. 2010, 12, 1004.
doi: 10.1021/ol1000186
Zapf, A.; Beller, M. Chem. Commun. 2005, 431.
(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.
Lundgren, R. J.; Hesp, K. D.; Stradiotto, M. Synlett 2011, 2443.
(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.
Liu, D.; Gao, W.; Dai, Q.; Zhang, X. Org. Lett. 2005, 7, 4907.
doi: 10.1021/ol051844w
Li, P.; Lu, B.; Fu, C.; Ma, S. Adv. Synth. Catal. 2013, 355, 1255.
doi: 10.1002/adsc.201300207
Handa, S.; Andersson, M. P.; Gallou, F.; Reilly, J.; Lipshutz, B. H. Angew. Chem., Int. Ed. 2016, 55, 4914.
doi: 10.1002/anie.201510570
(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.
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.
Wong, S. M.; So, C. M.; Chung, K. H.; Lau, C. P.; Kwong, F. Y. Eur. J. Org. Chem. 2012, 4172.
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.
Kwong, F. Y.; Chan, A. S. C. Synlett 2008, 1440.
(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.
(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.
Teo, S.; Weng, Z.; Hor, T. S. A. Organometallics 2006, 25, 1199.
doi: 10.1021/om050791j
(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.
(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.
Ullah, E.; McNulty, J.; Robertson, A. Tetrahedron Lett. 2009, 50, 5599.
doi: 10.1016/j.tetlet.2009.07.088
(a) Schaarschmidt, D.; Lang, H. Eur. J. Inorg. Chem. 2010, 4811.
(b) Schaarschmidt, D.; Lang, H. ACS Catal. 2011, 1, 411.
(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.
Armarego, W. L. F. Purification of Laboratory Chemicals, Butterworth-Heinemann, Oxford, UK, 2017.
Choy, P. Y.; Yuen, O. Y.; Leung, M. P.; Chow, W. K.; Kwong, F. Y. Eur. J. Org. Chem. 2020, 2846.
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
Wu, Y.; Choy, P. Y.; Kwong, F. Y. Org. Biomol. Chem. 2014, 12, 6820.
doi: 10.1039/C4OB01211A
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
McNulty, J.; Capretta, A.; Wilson, J.; Dyck, J.; Adjabeng, G.; Robertson, A. Chem. Commun. 2002, 1986.
So, C. M.; Lau, C. P.; Kwong, F. Y. Org. Lett. 2007, 9, 2795.
doi: 10.1021/ol070898y
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
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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Reaction conditions: 4-chlorotoluene (1.0 mmol), 2, 6-dimethylphenylboronic acid (1.5 mmol), Pd:ligand (1:3), K3PO4•H2O (3 mmol), and THF (3 mL) were stirred at 100 ℃ for 24 h under N2. Isolated yields of 3aa were reported full-stop