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SuFEx Chemistry of Thionyl Tetrafluoride (SOF 4 ) with Organolithium Nucleophiles: Synthesis of Sulfonimidoyl Fluorides, Sulfoximines, Sulfonimidamides, and Sulfonimidates
Author(s) -
Gao Bing,
Li Suhua,
Wu Peng,
Moses John E.,
Sharpless K. Barry
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201712145
Subject(s) - chemistry , nucleophile , thionyl chloride , sulfur , reactivity (psychology) , organic chemistry , inorganic chemistry , combinatorial chemistry , chloride , medicine , alternative medicine , pathology , catalysis
Thionyl tetrafluoride (SOF 4 ) is a valuable connective gas for sulfur fluoride exchange (SuFEx) click chemistry that enables multidimensional linkages to be created via sulfur–oxygen and sulfur–nitrogen bonds. Herein, we expand the available SuFEx chemistry of SOF 4 to include organolithium nucleophiles, and demonstrate, for the first time, the controlled projection of sulfur–carbon links at the sulfur center of SOF 4 ‐derived iminosulfur oxydifluorides (R 1 −N=SOF 2 ). This method provides rapid and modular access to sulfonimidoyl fluorides (R 1 −N=SOFR 2 ), another array of versatile SuFEx connectors with readily tunable reactivity of the S−F handle. Divergent connections derived from these valuable sulfonimidoyl fluoride units are also demonstrated, including the synthesis of sulfoximines, sulfonimidamides, and sulfonimidates.