Electrophilic tetraalkylammonium nitrate nitration. II. Improved anhydrous aromatic and heteroaromatic mononitration with tetramethylammonium nitrate and triflic anhydride,including selected microwave examples |
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Authors: | Shackelford Scott A Anderson Mark B Christie Lance C Goetzen Thomas Guzman Mark C Hananel Martha A Kornreich Wayne D Li Haitao Pathak Ved P Rabinovich Alex K Rajapakse Ranjan J Truesdale Larry K Tsank Stella M Vazir Haresh N |
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Institution: | Pfizer Global Research and Development, La Jolla Laboratories, 3550 General Atomics Court, San Diego, California 92121-1194, USA. scott.shackelford@pfizer.com |
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Abstract: | A new one-pot nitration employing tetramethylammonium nitrate and trifluoromethanesulfonic anhydride in dichloromethane to provide a ready source of the nitronium triflate nitrating agent is presented. Rapid and selective nitration with a variety of aromatic and heteroaromatic substrates is achieved resulting in the synthesis of several novel organic compounds. A distinct advantage is the removal of undesired byproducts by aqueous workup. This very mild nitration permits large-scale syntheses and gives high isolated product yields that often require no further purification. This tetramethylammonium nitrate-based nitration also has been applied to microwave-assisted conditions, and the results with several compounds are outlined. |
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