Electrophilic tetraalkylammonium nitrate nitration. II. Improved anhydrous aromatic and heteroaromatic mononitration with tetramethylammonium nitrate and triflic anhydride, including selected microwave examples

被引：57

作者：

Shackelford, SA ^{[1
]}

Anderson, MB ^{[1
]}

Christie, LC ^{[1
]}

Goetzen, T ^{[1
]}

Guzman, MC ^{[1
]}

Hananel, MA ^{[1
]}

Kornreich, WD ^{[1
]}

Li, HT ^{[1
]}

Pathak, VP ^{[1
]}

Rabinovich, AK ^{[1
]}

Rajapakse, RJ ^{[1
]}

Truesdale, LK ^{[1
]}

Tsank, SM ^{[1
]}

Vazir, HN ^{[1
]}

机构：

[1] Pfizer Global Res & Dev, La Jolla Labs, San Diego, CA 92121 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 02期

关键词：

D O I：

10.1021/jo026202q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：267 / 275

页数：9

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