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Molecules 2015, 20(12), 22757-22766; doi:10.3390/molecules201219881

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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Author to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 18 November 2015 / Revised: 7 December 2015 / Accepted: 11 December 2015 / Published: 19 December 2015
(This article belongs to the Section Organic Synthesis)
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Abstract

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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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

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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