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. Author manuscript; available in PMC: 2023 Jan 21.
Published in final edited form as: Angew Chem Int Ed Engl. 2021 Dec 7;61(4):e202112375. doi: 10.1002/anie.202112375

Scheme 1. BTMG-HMDS mediated ASCC reaction between a variety of SuFEx hubs and aryl or alkyl alcohols.

Scheme 1.

Reaction conditions: a) Aromatic sulfonyl fluoride (0.1 mmol), aryl alcohol (0.1 mmol), HMDS (0.1 mmol), and BTMG (1.0 mol%) stirred in MeCN for 5 min; b) Aromatic sulfonyl fluoride (0.1 mmol), alkyl alcohol (0.1 mmol), HMDS (0.1 mmol), and BTMG (20 mol%) stirred in MeCN for 30 min; c) Alkyl sulfonyl fluoride (0.2 mmol), aromatic alcohol (0.1 mmol), HMDS (0.1 mmol), and BTMG (20 mol%) stirred in MeCN under microwave irradiation for 30 min at 60 °C; d) Aryl alcohol (0.1 mmol), HMDS (0.1 mmol), and BTMG (5.0 mol%) were stirred in MeCN under an atmosphere of sulfuryl fluoride (balloon) for 15 min; e) Aryl fluorosulfate (0.1 mmol), aryl alcohol (0.1 mmol), HMDS (0.1 mmol), and BTMG (20 mol%) were stirred in MeCN for 30 min; f) Iminosulfur oxydifluoride (0.1 mmol), aryl alcohol (0.1 mmol), HMDS (0.1 mmol), and BTMG (5.0 mol%) were stirred in MeCN for 5 min; [a]Select examples shown, see Supporting Information for a full list of examples; [b]Reaction stirred for 30 min using 5.0 mol% BTMG; [c]Reaction stirred for 60 min using 10 mol% BTMG; [d] Reaction conducted on 0.2 mmol scale using 1.0 equiv of alkyl sulfonyl fluoride; [e]Conducted on a 50 mmol scale; [f]Reaction run for 20 min.