Pd-Nanoparticles-Catalyzed C(sp²)–H Arylation for the Synthesis of Functionalized Heterocycles: Recent Progress and Prospects

Abstract

Transition-metal-nanoparticles-catalyzed C–H activation/functionalization is a prominent topic in contemporary research, enabling the functionalization of privileged heterocyclic scaffolds that hold a significant space in the scientific community due to their immense applications in materials science and in medicinal, natural product, and agricultural chemistry. Among transition-metal-based nanoparticles, Pd nanoparticle catalysis has emerged as the most attractive tool for promoting a wide array of practical synthetic transformations of heterocycles. In the last few years, the catalytic application of Pd nanoparticles in C–H functionalization has gained popularity in generating relatively inaccessible bonds with a high degree of selectivity and efficiency via the activation of surface metal atoms at the nanoscale level. The quantum size effect of nanoparticles offers a large surface area, with typically many easily accessible active sites/unit areas. These unique characteristics of nanoparticles are considered primary factors of enhanced catalytic activity compared to bulk materials. The nanoparticle catalysts anchored on solid-supports plus unsupported types (e.g., magnetic nanoparticles) allow easy separation from the reaction mixture, enabling recycling multiple times, which contributes notably to sustainable management and cost efficiency of a production process. In the current review, we discuss Pd-nanoparticles-catalyzed C(sp²)–H arylation for the synthesis of functionalized heterocycles, covering literature reports from 2010 to 2021. The preparation of Pd nanoparticles and the mechanistic realizations in their corresponding reactions are also explained briefly.

1 Introduction

2 Arylation of Heterocyclic Scaffolds

2.1 Synthesis of Functionalized Indole Derivatives

2.2 Synthesis of Functionalized (Benzo)thiazole/Benzoxazole Derivatives

2.3 Synthesis of Functionalized Triazoles

2.4 Synthesis of Functionalized Pyridines and Related Scaffolds

2.5 Synthesis of Functionalized Furan, Thiophene and N-Methylpyrrole Scaffolds

2.6 Synthesis of Functionalized Multiple Heterocycles via Single-Step Strategies

3 Conclusions

Key words

Pd nanoparticles - binary nanoclusters - solid-support - heterogeneity - C(sp²)–H arylation - heterocycles - leaching - recoverability and recyclability

Publication History

Received: 31 January 2023

Accepted after revision: 22 March 2023

Accepted Manuscript online:
22 March 2023

Article published online:
03 May 2023

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Selected representative examples:
• 73a Stephan DW, Erker G. Chem. Sci. 2014; 5: 2625
• 73b Melen RL. Chem. Commun. 2014; 50: 1161
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Selected representative examples:
• 77a Osakada K, Nishihara Y. Dalton Trans. 2022; 51: 777
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• 82a Valiente A, Carrasco S, Sanz-Marco A, Tai C.-W, Gómez AB, Martín-Matute B. ChemCatChem 2019; 11: 3933
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Selected representative examples:
• 87a Tokala R, Mahajan S, Kiranmai G, Sigalapalli DK, Sana S, John SE, Nagesh N, Shankaraiah N. Bioorg. Chem. 2021; 106: 104481
• 87b Seth K, Purohit P, Chakraborti AK. Curr. Med. Chem. 2017; 24: 4638
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Selected representative examples:
• 94a Yan Y, Miao J, Yang Z, Xiao F.-X, Yang HB, Liu B, Yang Y. Chem. Soc. Rev. 2015; 44: 3295
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Selected representative examples:
• 96a Jang L.-W, Shim J, Son DI, Cho H, Zhang L, Zhang J, Menghini M, Locquet J.-P, Seo JW. Sci. Rep. 2019; 9: 12344
• 96b Luo Y, Wang K, Luo S, Zhao F, Wu H, Jiang K, Li Q, Fan S, Wang J. ACS Appl. Nano Mater. 2018; 1: 2997
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• 96d Sridhar V, Kim H.-J, Jung J.-H, Lee C, Park S, Oh I.-K. ACS Nano 2012; 6: 10562
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Selected representative examples:
• 100a Matin MM, Matin P, Rahman MR, Hadda TB, Almalki FA, Mahmud S, Ghoneim MM, Alruwaily M, Alshehri S. Front. Mol. Biosci. 2022; 9: 864286
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• 100e Costa MS, Boechat N, Rangel ÉA, da Silva FC, de Souza AM. T, Rodrigues CR, Castro HC, Junior IN, Lourenço MC. S, Wardell SM. S. V, Ferreira VF. Bioorg. Med. Chem. 2006; 14: 8644

Selected representative examples:
• 101a Dai J, Tian S, Yang X, Liu Z. Front Chem. 2022; 10: in press DOI: 10.3389/fchem.2022.891484.
• 101b Shiri P, Amani AM, Mayer-Gall T. Beilstein J. Org. Chem. 2021; 17: 1600
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Selected representative examples:
• 104a Sharma M, Prasher P. Synth. Commun. 2022; 52: 1337
• 104b Kwong HC, Kumar CS. C, Mah SH, Mah YL, Chia TS, Quah CK, Lim GK, Chandraju S. Sci. Rep. 2019; 9: 926
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Selected representative examples:
• 105a Reen GK, Kumar A, Sharma P. Beilstein J. Org. Chem. 2019; 15: 1612
• 105b Mu B, Wu Y, Li J, Zou D, Chang J, Wu Y. Org. Biomol. Chem. 2016; 14: 246
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Selected representative examples:
• 107a Kashid AA, Patil DJ, Mali RD, Patil VP, Neethu TV, Meroliya HK, Waghmode SA, Iyer S. Catal. Lett. 2021; 151: 353
• 107b Maize M, El-Boraey HA, Ayad MI, Holmes JD, Collins G. J. Catal. 2021; 585: 480
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• 107e Dhankhar A, Rai RK, Tyagi D, Yao X, Singh SK. ChemistrySelect 2016; 1: 3223
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Selected representative examples:
• 119a Yang Z, Yu J.-T, Pan C. Org. Biomol. Chem. 2021; 19: 8442
• 119b Gao P, Guo W, Xue J, Zhao Y, Yuan Y, Xia Y, Shi Z. J. Am. Chem. Soc. 2015; 137: 12231
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Selected representative examples:
• 120a Farokhi A, Shahroosvand H, Monache GD, Pilkington M, Nazeeruddin MK. Chem. Soc. Rev. 2022; 51: 5974
• 120b Li B, Seth K, Niu B, Pan L, Yang H, Ge H. Angew. Chem. Int. Ed. 2018; 57: 3401
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• 121 Li R, Zhou Y, Xu X, Dong G. J. Am. Chem. Soc. 2019; 141: 18958
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• 123a Köhler K, Heidenreich RG, Soomro SS, Pröckl SS. Adv. Synth. Catal. 2008; 350: 2930
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Selected representative examples:
• 125a Ueda K, Amaike K, Maceiczyk RM, Itami K, Yamaguchi J. J. Am. Chem. Soc. 2014; 136: 13226
• 125b Tamilavan V, Sakthivel P, Li Y, Song M, Kim C.-H, Jin S.-H, Hyun MH. J. Polym. Sci., Part A: Polym. Chem. 2010; 48: 3169
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Selected representative examples:
• 126a Cole DC, Stock JR, Chopra R, Cowling R, Ellingboe JW, Fan KY, Harrison BL, Hu Y, Jacobsen S, Jennings LD, Jin G, Lohse PA, Malamas MS, Manas ES, Moore WJ, O’Donnell M.-M, Olland AM, Robichaud AJ, Svenson K, Wu JJ, Wagner E, Bard J. Bioorg. Med. Chem. Lett. 2008; 18: 1063
• 126b Cole DC, Manas ES, Stock JR, Condon JS, Jennings LD, Aulabaugh A, Chopra R, Cowling R, Ellingboe JW, Fan KY, Harrison BL, Hu Y, Jacobson S, Jin G, Lin L, Lovering FE, Malamas MS, Stahl ML, Strand J, Sukhdeo MN, Svenson K, Turner MJ, Wagner E, Wu J, Zhou P, Bard J. J. Med. Chem. 2006; 49: 6158
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Selected representative examples:
• 131a Agrawal N, Mishra P. Med. Chem. Res. 2018; 27: 1309
• 131b Rao PS, Kurumurthy C, Veeraswamy B, Poornachandra Y, Kumar CG, Narsaiah B. Bioorg. Med. Chem. Lett. 2014; 24: 1349
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