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Open AccessFeature PaperArticle

OSU-6: A Highly Efficient, Metal-Free, Heterogeneous Catalyst for the Click Synthesis of 5-Benzyl and 5-Aryl-1H-tetrazoles

Department of Chemistry, Oklahoma State University, Stillwater, OK 74078-3071, USA
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Academic Editor: Derek J. McPhee
Molecules 2015, 20(12), 22757-22766; https://doi.org/10.3390/molecules201219881
Received: 18 November 2015 / Revised: 7 December 2015 / Accepted: 11 December 2015 / Published: 19 December 2015
(This article belongs to the Section Organic Chemistry)
OSU-6, an MCM-41 type hexagonal mesoporous silica with mild Brönsted acid properties, has been used as an efficient, metal-free, heterogeneous catalyst for the click synthesis of 5-benzyl and 5-aryl-1H-tetrazoles from nitriles in DMF at 90 °C. This catalyst offers advantages including ease of operation, milder conditions, high yields, and reusability. Studies are presented that demonstrate the robust nature of the catalyst under the optimized reaction conditions. OSU-6 promotes the 1,3-dipolar addition of azides to nitriles without significant degradation or clogging of the nanoporous structure. The catalyst can be reused up to five times without a significant reduction in yield, and it does not require treatment with acid between reactions. View Full-Text
Keywords: 5-benzyl and 5-aryl-1H-tetrazoles; carboxylic acid bioisosteres; click 1,3-dipolar addition; heterogeneous catalysis; recyclable catalyst 5-benzyl and 5-aryl-1H-tetrazoles; carboxylic acid bioisosteres; click 1,3-dipolar addition; heterogeneous catalysis; recyclable catalyst
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Nammalwar, B.; Muddala, N.P.; Pitchimani, R.; Bunce, R.A. OSU-6: A Highly Efficient, Metal-Free, Heterogeneous Catalyst for the Click Synthesis of 5-Benzyl and 5-Aryl-1H-tetrazoles. Molecules 2015, 20, 22757-22766.

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