A Green Nanopalladium-Supported Catalyst for the Microwave-Assisted Direct Synthesis of Xanthones

H. Sebastián Steingruber; Pamela Mendioroz; Alejandra S. Diez; Darío C. Gerbino

doi:10.1055/s-0039-1691069

Synthesis, Table of Contents

Synthesis 2020; 52(04): 619-628
DOI: 10.1055/s-0039-1691069

paper

A Green Nanopalladium-Supported Catalyst for the Microwave-Assisted Direct Synthesis of Xanthones

Authors

H. Sebastián Steingruber
Pamela Mendioroz
Alejandra S. Diez
Darío C. Gerbino∗

Instituto de Química del Sur, INQUISUR (CONICET-UNS), Departamento de Química, Universidad Nacional del Sur, Avenida Alem 1253, 8000 Bahía Blanca, Argentina Email: dgerbino@uns.edu.ar

Abstract

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Abstract

We report an efficient, selective, rapid and eco-friendly protocol for the one-step synthesis of a small xanthone library via an intermolecular catalytic coupling from readily available salicylaldehydes and 1,2-dihaloarenes under ligand-free conditions. To achieve this advantageous direct annulation, we used a novel recoverable palladium nanocatalyst supported on a green biochar under microwave irradiation. Unlike other existing palladium-based approaches, our synthetic strategy showed a greater operational simplicity, drastic reduction in reaction times, and an excellent tolerance to diverse functional groups. The reaction proceeds in very good yields and with high regioselectivity. The novel heterogeneous catalyst can be recycled and reused up to four times without significant loss of activity.

Key words

xanthones - coupling - microwave-assisted synthesis - palladium nanoparticles - green biochar

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References

References and Notes
1 Hepworth JD. In Comprehensive Heterocyclic Chemistry . Pergamon; Oxford: 1984: 3

2a Masters KS, Bräse S. Chem. Rev. 2012; 112: 3717
2b Vierira LM. M, Kijjoa A. Curr. Med. Chem. 2005; 12: 2413

3a Sousa E, Pinto MM. Curr. Med. Chem. 2005; 12: 24472
3b Suzuki Y, Fukuta Y, Ota S, Kamiya M, Sato M. J. Org. Chem. 2011; 76: 3960
3c Barbero N, SanMartin R, Domínguez E. Green Chem. 2009; 11: 830
3d Cardona ML, Fernández MJ, Pedro JR, Serrano A. Photochemistry 1990; 29: 3003
3e Woo S, Jung J, Lee C, Kwon Y, Na Y. Bioorg. Med. Chem. Lett. 2007; 17: 1163

4a Menéndez CA, Biscussi B, Accordino RS, Murray AP, Appignanesi GA, Gerbino DC. Bioorg. Chem. 2017; 75: 201
4b Shagufta W, Ahmad I. Eur. J. Med. Chem. 2016; 116: 267

5a Holleman AF. Org. Synth. 1927; 7: 84
5b Blatt AH. Org. React. 1942; 1: 342
5c Berlinger E. Org. React. 1949; 5: 229
5d Grover PK, Shah GD, Shah RC. J. Chem. Soc. 1955; 3982
5e Quillinan A, Scheinmann F. J. Chem. Soc., Perkin Trans. 1 1973; 1329
5f Jackson WT, Robert JB, Froelich LL, Gapinski DM, Mallett BE, Sawyer JS. J. Med. Chem. 1993; 36: 1726
5g Familoni OB, Ionica I, Bower JF, Snieckus V. Synlett 1997; 1081
5h Hassal CH, Lewis JR. J. Chem. Soc. 1961; 2312
5i Murashige R, Hayashi Y, Ohmori S, Torii A, Aizu Y, Muto Y, Murai Y, Oda Y, Hashimoto M. Tetrahedron 2011; 67: 641

For some recent synthetic xanthone routes, see:

6a Tang J, Zhao S, Wei Y, Quan Z, Huo C. Org. Biomol. Chem. 2017; 15: 1589
6b Venkanna A, Vinod K, Goud P, Prasad PV, Shanker M, Rao PV. ChemistrySelect 2016; 1: 2271
6c Rao ML. N, Ramakrishna BS. RSC Adv. 2016; 6: 75505
6d Shen C, Wu XF. Synlett 2016; 27: 1269
6e Wang S, Xie K, Tan Z, An X, Zhou X, Guo CC, Peng Z. Chem. Commun. 2009; 42: 6469
6f Zhao J, Larock RC. Org. Lett. 2005; 7: 4273
6g Zhao J, Larock RC. J. Org. Chem. 2007; 72: 583
6h Wertz S, Leifert D, Studer A. Org. Lett. 2013; 15: 928
6i Yang J, Dong C, Li H, Li Y. Chin. Sci. Bull. 2012; 57: 2364
6j Wang P, Rao H, Hua R, Li CJ. Org. Lett. 2012; 14: 902
6k Manna SK, Lavanya S, Manda K, Panda G. Tetrahedron Lett. 2014; 55: 5759
6l Zhang H, Shi R, Gan P, Liu C, Ding A, Wang Q, Lei A. Angew. Chem. Int. Ed. 2012; 51: 5204
6m Xu Y, Zhou J, Zhang C, Chen K, Zhang T, Du Z. Tetrahedron Lett. 2014; 55: 6432
6n Genovese S, Fiorito S, Specchiulli MC, Taddeo VA, Epifano F. Tetrahedron Lett. 2015; 56: 847
6o Hu J, Adogla EA, Ju Y, Fan D, Wang Q. Chem. Commun. 2012; 48: 11256
6p Rao H, Ma X, Liu Q, Li Z, Cao S, Li CJ. Adv. Synth. Catal. 2013; 355
6q Suzuki Y, Fukuta Y, Ota S, Kamiya M, Sato M. J. Org. Chem. 2011; 76: 3960
6r Jiang N, Li SY, Xie SS, Yao H, Sun H, Wang XB, Kong LY. RSC Adv. 2014; 4: 63632
6s Barbero N, San Martin R, Domínguez E. Green Chem. 2009; 11: 830
6t Hintermann L, Masuo R, Suzuki K. Org. Lett. 2008; 10: 4859
6u Woydziak ZR, Fu L, Peterson BR. J. Org. Chem. 2012; 77: 473
6v Johnson MM, Naidoo JM, Fernandes MA, Mmutlane EM, van Otterlo WA, de Koning BA. J. Org. Chem. 2010; 75: 8701

7a Hemalatha K, Madhumitha G, Kajbafvala A, Anupama N, Sompalle R, Roopan MS. J. Nanomater. 2013; 341015
7b Polshettiwar R, Varma S. Green Chem. 2010; 12: 743
7c Astruc D. Nanoparticles and Catalysis . Wiley-VCH; Weinheim: 2008. Chap. 1

8a Sosnik A, Gotelli G, Abraham GA. Prog. Polym. Sci. 2011; 36: 1050
8b Kappe CO. Chem. Soc. Rev. 2008; 37: 1127

9 Atwood DA. Sustainable Inorganic Chemistry . Wiley-VCH; Weinheim: 2016: 333

10a Menéndez CA. Doctoral Dissertation . Universidad Nacional del Sur; Argentina: 2018
10b Scoccia J, Castro MJ, Faraoni MA, Bouzat C, Martín VS, Gerbino DC. Tetrahedron 2017; 73: 2913
10c Menéndez C, Nador F, Radivoy G, Gerbino DC. Org. Lett. 2014; 16: 2846
10d Sierra MB, Alarcón L, Gerbino DC, Pedroni VI, Buffo FE, Morini MA. Chem. Phys. Lipids 2017; 206

11a Ruan J, Saidi O, Iggo JA, Xiao J. J. Am. Chem. Soc. 2008; 130: 10510
11b Satoh T, Itaya T, Miura M, Nomura M. Chem. Lett. 1996; 823
11c Álvarez-Bercedo P, Flores-Gaspar A, Correa A, Martin R. J. Am. Chem. Soc. 2010; 132: 466
11d Solé D, Mariani F. J. Org. Chem. 2013; 78: 8136
11e Nowrouzi N, Motevalli S, Tarokh D. J. Mol. Catal. A: Chem. 2015; 396: 224
11f Solé D, Mariani F, Fernández I. Eur. J. Org. Chem. 2015; 3935

12a Casoni AI, Bidegain M, Cubitto M, Curvetto N, Volpe M. Bioresour. Technol. 2014; 177: 406
12b Casoni AI, Hoch PM, Volpe M, Gutierrez VJ. J. Cleaner Prod. 2018; 178: 237

13 For a very interesting review on transition-metal-catalyzed site-selective cross-coupling reactions of di- and polyhalogenated compounds, see: Wang JR, Manabe K. Synthesis 2009; 1405

14a Solé D, Mariani F. J. Org. Chem. 2013; 78: 8136
14b Tsuda T, Satoh T, Miura M. Chem. Lett. 1997; 1103
14c Satoh T, Inoh JC, Kawamura Y, Miura M, Nomura M. Bull. Chem. Soc. Jpn. 1998; 71: 2239
14d Satoh T, Kametani Y, Terao Y, Miura M, Nomura M. Angew. Chem., Int. Ed. Engl. 1997; 36: 1740
14e Kawamura Y, Satoh T, Miura M, Nomura M. Chem. Lett. 1999; 961

15 Satoh T, Itaya T, Miura M, Nomura M. Chem. Lett. 1996; 823
16 Perrin DD, Amarego WL. F. Purification of Laboratory Chemicals . Pergamon; Oxford: 1988
17 Schölten JF, Pijpers AP, Hustings ML. Catal. Rev.: Sci. Eng. 1985; 27: 151
18 Mozingo R. Org. Synth. 1955; 3: 685
19 Gardikis Y, Tsoungas PG, Potamitis C, Zervou M, Cordopatis P. Heterocycles 2011; 83: 1077
20 Zhao J, Yue D, Campo MA, Larock RC. J. Am. Chem. Soc. 2007; 129: 5288
21 Cremins PJ, Saengchantara ST, Wallace TW. Tetrahedron 1987; 43: 3075
22 Fremeau T, White RD. Jr, Patel VF. J. Med. Chem. 2014; 57: 9796
23 Granoth I, Pownall HJ. J. Org. Chem. 1975; 40: 2088
24 Dhar SN. J. Chem. Soc., Trans. 1920; 117: 1053

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