Journal
CHEMSUSCHEM
Volume 15, Issue 18, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cssc.202201000
Keywords
beta-aminosulfonyl fluorides; aza-Michael addition; N-heterocyclic carbenes; organocatalysis; water chemistry
Funding
- Ministry of Science, ICT and Future Planning of Korea [2020R1C1C1006440, 2020R1A4A1018019]
- Korea Basic Science Institute (National research Facilities and Equipment Center) - Ministry of Education [2022R1A6C101A751]
- National Research Foundation of Korea [2020R1A4A1018019, 2022R1A6C101A751, 2020R1C1C1006440] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
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A water-accelerated, N-heterocyclic carbene (NHC)-catalyzed aza-Michael addition reaction was reported for the synthesis of beta-aminosulfonyl fluorides, key components of the SuFEx reaction. Water as a reaction medium significantly enhanced the reaction rate and demonstrated late-stage ligation with bioactive molecules.
Herein, a water-accelerated, N-heterocyclic carbene (NHC)-catalyzed aza-Michael addition reaction was reported to access beta-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 beta-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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