NiNP@rGO Nanocomposites as Heterogeneous Catalysts for Thiocarboxylation Cross-Coupling Reactions

Lorenzo Lombardi; Raffaello Mazzaro; Massimo Gazzano; Alessandro Kovtun; Vittorio Morandi; Giulio Bertuzzi; Marco Bandini

doi:10.1055/a-1669-0944

Synthesis, Table of Contents

Synthesis 2022; 54(06): 1633-1642
DOI: 10.1055/a-1669-0944

paper

NiNP@rGO Nanocomposites as Heterogeneous Catalysts for Thiocarboxylation Cross-Coupling Reactions

Authors

Lorenzo Lombardi

^aDipartimento di Chimica ‘Giacomo Ciamician’, Alma Mater Studiorum, Università di Bologna, Via Selmi 2, Bologna, Italy
Raffaello Mazzaro

^bCNR-IMM, Via Piero Gobetti 101, 40129 Bologna, Italy

^cDipartimento di Fisica e Astronomia ‘A. Righi’, Alma Mater Studiorum, Università di Bologna, Via Berti Pichat 6/2, Bologna, Italy
Massimo Gazzano

^dIstituto per la Sintesi Organica e Fotoreattività (ISOF) – CNR, Via Gobetti 101, 40129 Bologna, Italy
Alessandro Kovtun

^dIstituto per la Sintesi Organica e Fotoreattività (ISOF) – CNR, Via Gobetti 101, 40129 Bologna, Italy
Vittorio Morandi

^bCNR-IMM, Via Piero Gobetti 101, 40129 Bologna, Italy

^cDipartimento di Fisica e Astronomia ‘A. Righi’, Alma Mater Studiorum, Università di Bologna, Via Berti Pichat 6/2, Bologna, Italy
Giulio Bertuzzi

^aDipartimento di Chimica ‘Giacomo Ciamician’, Alma Mater Studiorum, Università di Bologna, Via Selmi 2, Bologna, Italy
Marco Bandini∗

^aDipartimento di Chimica ‘Giacomo Ciamician’, Alma Mater Studiorum, Università di Bologna, Via Selmi 2, Bologna, Italy

Abstract

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Abstract

A new type of ligand-free Ni-nanoparticles supported on rGO (size distribution average d = 9 ± 3 nm) was prepared and fully characterized via morphological (Fe-SEM), structural (P-XRD, HR-TEM), and spectroscopic (ICP-EOS, XPS) analysis tools. The metal composite was effectively employed in the unprecedented heterogeneously Ni-assisted cross-coupling reaction of aryl/vinyl iodides and thiocarboxylates. A range of sulfur-containing aryl as well as vinyl derivatives (15 examples) was achieved in high yields (up to 82%), under mild reaction conditions, and with wide functional group tolerance.

Key words

heterogeneous catalysis - Ni-nanoparticles - cross-coupling - thiocarboxylation

Full Text

References

References
1 For general reviews see: Johansson Seechurn CC. C, Kitching MO, Colacot TJ, Snieckus V. Angew. Chem. Int. Ed. 2012; 51: 5062

2a Tasker SZ, Standley EA, Jamison TF. Nature 2014; 509: 299
2b Hazari N, Melvin PR, Beromi MM. Nat. Rev. Chem. 2017; 1: 0025
2c Yaqiong L, Yuhang F, Qianfa J. Chin. J. Org. Chem. 2019; 39: 350
2d Nebra N. Molecules 2020; 25: 1141
2e Zhu C, Yue H, Jia J, Rueping M. Angew. Chem. Int. Ed. 2021; 60: 17810

3a Liu L, Corma A. Chem. Rev. 2018; 118: 4981
3b Ndoloming MJ, Bingwa N, Meijboom R. J. Mater. Sci. 2020; 55: 6195
3c Jaji N.-D, Lee HL, Hussin MH, Akil HM, Zakaria M, Hafi Othman MB. Nanotech. Rev. 2020; 9: 1456

For a collection of representative examples see:

4a Bhowmik K, Sengupta D, Basu B, De G. RSC Adv. 2014; 4: 35442
4b Hussain N, Gogoi P, Khare P, Das MR. RSC Adv. 2015; 5: 103105
4c Keyhaniyan M, Shiri A, Eshighi H, Khojastehnezhad A. New J. Chem. 2018; 42: 19433
4d Bathla A, Patil B. ChemistrySelect 2018; 3: 4738
4e Dong Y, Jv J.-J, Li Y, Li W.-H, Chen Y.-Q, Sun Q, Ma J.-P, Dong Y.-B. RSC Adv. 2019; 9: 20266
4f Adam AA, Szabados M, Polyakovics A, Konya Z, Kukovecz A, Sipos P, Palinko I. J. Nanosci. Nanotechnol. 2019; 19: 453
4g Li Y, Hu Y, Shi F, Li H, Xie W, Chen J. Angew. Chem. Int. Ed. 2019; 58: 9049
4h Naeimi H, Kiani F. J. Organomet. Chem. 2019; 885: 65
4i Nan L, Yalan C, Jixiang L, Dujuan O, Wenhui D, Rouhi J, Mustapha M. RSC Adv. 2020; 10: 27923
4j Ádám AA, Szabados M, Varga G, Papp A, Musza K, Kónya Z, Kukovecz A, Sipos P, Pálinkó I. Nanomaterials 2020; 10: 632
4k Raoufi F, Manojjemi M, Aghaei H, Zare K, Ghaedi M. ChemistrySelect 2020; 5: 211
4l Murugan K, Nainamalai D, Kanagaraj P, Nagappan SG, Palaniswamy S. Appl. Organomet. Chem. 2020; 34: e5778
4m Keyhaniyan M, Khojastehnezhad A, Eshighi H, Shiri A. Appl. Organomet. Chem. 2021; 35: e6158
4n Bhakta S, Ghosh T. ChemCatChem 2021; 13: 828 ; and references therein

5 Łastawiecka E, Flis A, Stankevič M, Greluk M, Słowikb G, Gac W. Org. Chem. Front. 2018; 5: 2079

6a Platon M, Wijaya N, Rampazzi V, Cui L, Rousselin Y, Saeys M, Hierse J.-C. Chem. Eur. J. 2014; 20: 12584
6b Sengupta D, Bhowmik K, De G, Basu B. Beilstein J. Org. Chem. 2017; 13: 1796

7 Wang N, Saidhreddy P, Jiang X. Nat. Prod. Rep. 2020; 37: 246

8a Lee C.-F, Liu Y.-C, Badsara SS. Chem. Asian J. 2014; 9: 706 ; and references therein
8b Taherinia Z, Ghorbani-Choghamarani A. Can. J. Chem. 2019; 97: 46
8c Panigrahi R, Sahu SK, Behera PK, Panda S, Rout L. Chem. Eur. J. 2020; 26: 620
8d Panda S, Sahu SK, Behera PK, Panigrahi R, Garnaik B, Rout L. New J. Chem. 2020; 44: 2500
8e Annamalai P, Liu K.-C, Badsara SS, Lee C.-F. Chem. Rec. 2021; in press

For electrochemical tools in oxidative C–S cross-coupling reaction see:

8f Song C, Liu K, Dong X, Chiang C.-W. Synlett 2019; 30: 1149

9a Favaretto L, An J, Sambo M, De Nisi A, Bettini C, Melucci M, Kovtun A, Liscio A, Palermo V, Bottoni A, Zerbetto F, Calvaresi M, Bandini M. Org. Lett. 2018; 20: 3705
9b Lombardi L, Bellini D, Bottoni A, Calvaresi M, Monari M, Kovtun A, Palermo V, Melucci M, Bandini M. Chem. Eur. J. 2020; 26: 10427

10a Ji Z, Shen X, Zhu G, Zhou H, Yuan Z. J. Mater. Chem. 2012; 22: 3471
10b Nabid MR, Bide Y, Dastar F. Catal. Lett. 2015; 145: 1798
10c Liu Y, Gao C, Li Q, Pang H. Chem. Eur. J. 2019; 25: 2141
10d Al-Nafiey A, Al-Mamoori MH. K, Alshrefi SM, Shakir AK, Ahmed RT. Mater. Today: Proc. 2019; 19: 94
10e Zhang X, Chen K.-H, Zhou Z.-H, He L.-H. ChemCatChem 2020; 12: 4825

11 Parodi A, Battaglioli S, Liu Y, Monari M, Marín-Luna M, Silva López C, Bandini M. Chem. Commun. 2019; 55: 9669

12a Peng K, Gao M.-Y, Yi Y.-Y, Guo J, Dong Z.-B. Eur. J. Org. Chem. 2020; 2020: 1665
12b Sundaravelu N, Sangeetha S, Sekar G. Org. Biomol. Chem. 2021; 19: 1459

For examples of homogeneous metal-catalyzed thiocarboxylation reaction see:

13a Lai C, Backes BJ. Tetrahedron Lett. 2007; 48: 3033
13b van den Hoogenband A, Lange JH. M, Broger RP. J, Stoit AR, Terpstra JW. Tetrahedron Lett. 2010; 51: 6877
13c Park N, Park K, Jang M, Lee S. J. Org. Chem. 2011; 76: 4371
13d Sonica-Castro SM, Peñéñory AB. Beilstein J. Org. Chem. 2013; 9: 467
13e Soria-Castro SM, Andrada DA, Caminos DA, Argüello JE, Robert M, Peñéñory AB. J. Org. Chem. 2017; 82: 11464
13f Olivito F, Costanzo P, Di Gioia ML, Nardi M, Oliverio M, Procopio A. Org. Biomol. Chem. 2018; 16: 7753

14 Mazzaro R, Boni A, Valenti G, Marcaccio M, Paolucci F, Ortolani L, Morandi V, Ceroni P, Bergamini G. ChemistryOpen 2015; 4: 268
15 Kim KS, Winograd N. Surf. Sci. 1974; 43: 625
16 Zhang Z, Matsubayashi Z, Grisafe A, Lee B, Lloyd JR. Mater. Chem. Phys. 2016; 170: 175
17 Kovtun A, Jones D, dell’Elce S, Treossi E, Liscio A, Palermo V. Carbon 2019; 143: 268
18 See the Supporting Information for a complete list of reaction condition screening.
19 Nasrallah HO, Min Y, Lerayer E, Nguyen T.-A, Poinsot D, Roger J, Brandés S, Heintz O, Roblin P, Jolibois F, Poteau R, Coppel Y, Kahn ML, Gerber IC, Axet MR, Serp P, Hierso J.-C. JACS Au 2021; 1: 187
20 Sweeney JB, Ball AK, Smith LJ. Chem. Eur. J. 2018; 24: 7354
21 Optimal reaction conditions involving NiNP-Type 2 required ca. 25 mol% of Ni loading with respect to 1.
22 The present catalytic protocol displayed marked counterion dependance. In fact, sodium and cesium thioacetates proved inefficiency in the coupling protocol.
23 Sun R, Qin Y, Nocera DG. Angew. Chem. Int. Ed. 2020; 59: 9527

24a Uchiyama M, Furuyama T, Kobayashi M, Matsumoto Y, Tanaka K. J. Am. Chem. Soc. 2006; 128: 8404
24b Bull SR, Palmer LC, Fry NJ, Greenfield MA, Messmore BW, Meade TJ, Stupp SI. J. Am. Chem. Soc. 2008; 130: 2742
24c Lee K, Ban HS, Naik R, Hong YS, Son S, Kim B.-K, Xia Y, Song KB, Lee H.-S, Won M. Angew. Chem. Int. Ed. 2013; 52: 10286
24d Melissaris AP, Litt MH. J. Org. Chem. 1994; 59: 5818
24e Soltani Y, Wilkins LC, Melen RL. Angew. Chem. Int. Ed. 2017; 56: 11995
24f Xu R.-S, Yue L, Pan Y.-J. Tetrahedron 2012; 68: 5046

25a Liu H, Zhao L, Yuan Y, Xu Z, Chen K, Qiu S, Tan H. ACS Catal. 2016; 6: 1732
25b Jixian P, Hui W, Zhongdong S. CN 107840815 A, 2018 . Add 370 mL of methanol to a 1000 mL four-necked flask. Add 370 mL of ethanol and 51.4 g of thiobenzoic acid. Add 19.0 g of potassium hydroxide. The reaction was vigorously stirred at 50 °C for 2.5 hours. Concentrate the reaction to a yellow solid. Wash with 200 mL of diethyl ether. 59.4 g of potassium thiobenzoate was filtered; yield: 99%.

Supplementary Material

Supporting Information (PDF) (opens in new window)