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Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
β-Aminosulfonyl Fluorides via Water-Accelerated N-Heterocyclic Carbene Catalysis
Jin Hyun Park1, Sun Bu Lee1, Byeong Jun Koo1
1Department of Chemistry, Sungkyunkwan University, Suwon, 16419 (Republic of, Korea.
Abstract:
Herein, a water-accelerated, N-heterocyclic carbene (NHC)-catalyzed aza-Michael addition reaction was reported to access β-aminosulfonyl fluorides, which are key hubs of the sulfur(VI) fluoride exchange (SuFEx) reaction. As a crucial reaction medium, water considerably enhanced the reaction rate with excellent chemo- and site-selectivity (up to >99 : 1) compared to conventional solvents. In addition, the late-stage ligation of bioactive molecules with the aliphatic β-amino SuFEx hub was demonstrated. Mechanistic studies on experimental, analytical, and computational approaches support noncovalent activation over NHC catalysis "on-water".
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