1202255-11-5Relevant academic research and scientific papers
SuFEx Chemistry of Thionyl Tetrafluoride (SOF4) with Organolithium Nucleophiles: Synthesis of Sulfonimidoyl Fluorides, Sulfoximines, Sulfonimidamides, and Sulfonimidates
Gao, Bing,Li, Suhua,Wu, Peng,Moses, John E.,Sharpless, K. Barry
, p. 1939 - 1943 (2018/01/22)
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.
C-H activation in S-alkenyl sulfoximines: An endo 1,5-hydrogen migration
Gao, Xuefeng,Gaddam, Vikram,Altenhofer, Erich,Tata, Rama Rao,Cai, Zhengxin,Yongpruksa, Nattawut,Garimallaprabhakaran, Aswin K.,Harmata, Michael
supporting information; experimental part, p. 7016 - 7019 (2012/10/07)
Intramolecular redox reaction: Heating N-alkyl, N-allyl-, and N-benzyl-substituted S-alkenyl sulfoximines under appropriate conditions results in the formation of NH-S-alkyl sulfoximines. The intramolecular redox reaction involves a hydride transfer that occurs by a 6-endo-trig process. The intermediates in the reaction can also give access to four- and six-membered heterocyclic rings and a new class of chiral dienes. Copyright
