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. 2018 Feb 12;57(7):1939-1943.
doi: 10.1002/anie.201712145. Epub 2018 Jan 16.

SuFEx Chemistry of Thionyl Tetrafluoride (SOF 4 ) With Organolithium Nucleophiles: Synthesis of Sulfonimidoyl Fluorides, Sulfoximines, Sulfonimidamides, and Sulfonimidates

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SuFEx Chemistry of Thionyl Tetrafluoride (SOF 4 ) With Organolithium Nucleophiles: Synthesis of Sulfonimidoyl Fluorides, Sulfoximines, Sulfonimidamides, and Sulfonimidates

Bing Gao et al. Angew Chem Int Ed Engl. .
Free PMC article

Abstract

Thionyl tetrafluoride (SOF4 ) 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 SOF4 to include organolithium nucleophiles, and demonstrate, for the first time, the controlled projection of sulfur-carbon links at the sulfur center of SOF4 -derived iminosulfur oxydifluorides (R1 -N=SOF2 ). This method provides rapid and modular access to sulfonimidoyl fluorides (R1 -N=SOFR2 ), 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.

Keywords: SuFEx chemistry; click chemistry; organolithium reagents; sulfonimidoyl fluorides; thionyl tetrafluoride.

Conflict of interest statement

Conflict of Interest

A patent application covering this work has been filed by The Scripps Research Institute (TSRI, PCT Patent Application No. PCT/US2017/063746).

Figures

Figure 1
Figure 1
(A) Sulfur–heteroatom links enabled connections at the SOF4 hub; (B) Sulfur-carbon link(s) enabled connections at the SOF4 hub; (C) Conventional route to sulfonimidoyl fluorides.

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