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Letters in Organic Chemistry

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ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

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Research Article

Facile Access to 2-Substituted Benzoxazoles Using Sawdust Supported N-Heterocyclic Carbene-Ni Complex via C-H Activation

Author(s): Dolly Kale, Gajanan Rashinkar, Audumbar Patil, Arjun Kumbhar and Rajashri Salunkhe*

Volume 17, Issue 6, 2020

Page: [479 - 489] Pages: 11

DOI: 10.2174/1570178616666190705153927

Price: $65

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Abstract

Sawdust supported N-heterocyclic carbene-nickel complex has been prepared by covalent grafting of 1-methyl imidazole in the matrix of chloropropyl modified sawdust followed by reaction with nickel acetate. The resultant NHC-Ni complex was employed as a heterogeneous catalyst for the synthesis of 2-substituted benzoxazoles from benzoxazole and aryl boronic acids following C-H activation strategy. The recycling experiments showed that the complex could be reused for five consecutive runs without significant loss in the yield of products.

Keywords: C-H activation, N-Heterocyclic carbene, sawdust, benzoxazole, reusability, heterogeneous analogues.

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[1]
(a)Ofele, K.J. J. Organomet. Chem., 1968, 12, 42-43.
[http://dx.doi.org/10.1016/S0022-328X(00)88691-X]]
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[http://dx.doi.org/10.1002/anie.196801412]]
(c)Díez-González, S.; Marion, N.; Nolan, S.P. Chem. Rev., 2009, 109(8), 3612-3676.
[http://dx.doi.org/10.1021/cr900074m] [PMID: 19588961]
(d)Fortman, G.C.; Nolan, S.P. J. Curr. Org. Chem., 2014, 18, 700-718.
[2]
(a)Velazquez, H.D.; Verpoort, F. Chem. Soc. Rev., 2012, 41(21), 7032-7060.
[http://dx.doi.org/10.1039/c2cs35102a] [PMID: 22842861]
(b)Díez-González, S.; Marion, N.; Nolan, S.P. Chem. Rev., 2009, 109(8), 3612-3676.
[http://dx.doi.org/10.1021/cr900074m] [PMID: 19588961]
(c)Cai, X-H.; Xie, B. Mini Rev. Org. Chem., 2018, 15, 248-260.
[http://dx.doi.org/10.2174/1570193X14666171018150710]
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[http://dx.doi.org/10.1016/j.ccr.2006.10.004]]
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[http://dx.doi.org/10.1039/C1CC16184A] [PMID: 22089808]
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[http://dx.doi.org/10.1002/adsc.201800459]
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[12]
Hu, W-Y.; Wang, P-P.; Zhang, S-L. Synthesis, 2015, 47, 42-48.
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