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

Gao, B., Li, S., Wu, P., Moses, J. E., Sharpless, K. B. (February 2018) SuFEx Chemistry of Thionyl Tetrafluoride (SOF(4) ) with Organolithium Nucleophiles: Synthesis of Sulfonimidoyl Fluorides, Sulfoximines, Sulfonimidamides, and Sulfonimidates. Angew Chem Int Ed Engl, 57 (7). pp. 1939-1943. ISSN 1433-7851 (Print)1433-7851

URL: https://pubmed.ncbi.nlm.nih.gov/29314580/
DOI: 10.1002/anie.201712145

Abstract

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.

Item Type: Paper
Additional Information: Angewandte Chemie (International ed. in English)
CSHL Authors:
Communities: CSHL labs > Moses lab
Depositing User: Matthew Dunn
Date: 12 February 2018
Date Deposited: 08 Jan 2021 17:27
Last Modified: 08 Jan 2021 17:27
PMCID: PMC6005182
URI: https://repository.cshl.edu/id/eprint/39577

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