Synthesis of Ngai Reagent and Longer Carbon Chain Variants for Perfluoroalkoxylations.

Org Lett

Department of Nanopharmaceutical Sciences, and Department of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555, Japan.

Published: December 2024

AI Article Synopsis

  • A new and simple method has been developed for making Ngai trifluoromethoxy and longer carbon chain variants, increasing options for perfluoroalkoxylation reactions.
  • The process uses inexpensive sodium perfluoroalkane sulfinates and hydroxylamines to enable efficient cross-coupling reactions with cerium(IV) ammonium nitrate (CAN), eliminating the need for expensive transition-metal catalysts.
  • This methodology works well for creating both Ngai-type radical and Qing-type nucleophilic perfluoroalkoxylation reagents.

Article Abstract

We present a straightforward method for the synthesis of Ngai trifluoromethoxy reagent and longer carbon chain variants, thereby expanding the range of options for perfluoroalkoxylation reactions. Utilizing cost-effective sodium perfluoroalkane sulfinates (RSONa) and -hydroxylamines, we achieved efficient oxidative cross-coupling reactions facilitated by cerium(IV) ammonium nitrate (CAN) without the need for transition-metal catalysts. The methodology proved effective not only for the synthesis of Ngai-type radical perfluoroalkoxylation reagents but also Qing-type nucleophilic perfluoroalkoxylation reagents.

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http://dx.doi.org/10.1021/acs.orglett.4c04170DOI Listing

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Department of Nanopharmaceutical Sciences, and Department of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555, Japan.

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