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. Author manuscript; available in PMC: 2021 Jul 20.
Published in final edited form as: Angew Chem Int Ed Engl. 2020 Jun 4;59(30):12460–12469. doi: 10.1002/anie.202003219

Scheme 2.

Scheme 2.

Reaction of SASF hubs with a selection of 1,3-dipoles, 1,5-dipoles, and dienes to assemble the SuFExable 173 compound DOC library 4a) 3,5-disubstituted isoxazole-4-sulfonyl fluorides [1.00 eq. SASF hub, 1.00 eq. imidoyl chloride, 2.00 eq. Et3N stirring in toluene at r.t., 10 min]; 4b) 2-methyl-3,5-disubstituted-2,3-dihydroisoxazole-4-sulfonyl fluorides [1.00 eq. SASF hub, 1.00 eq. nitrone stirring in CH2Cl2 at r.t., 30 min]; 4c) 1,5-disubstituted-1H-1,2,3-triazole-4-sulfonyl fluorides [1.00 eq. SASF hub, 1.00 eq. azide, 2.50 mol% [Rh(CO)2Cl]2 heating in DCE at 40 °C, 16 h]; 4d) 1,3,5-trisubstituted-1H-pyrazole-4-sulfonyl fluorides [2.00 eq. SASF hub, 1.00 eq. hydrazonoyl chloride, 1.50 eq. DIPEA stirring in MeCN at r.t., 1 h]; 4e) 1,3,5-trisubstituted-1H-pyrazole-4-sulfonyl fluorides [1.00 eq. SASF hub, 1.00 eq. Sydnone heating in toluene at 120 °C, 16 h]; 4f) 1,2,4-1H-pyrrole-3-sulfonyl fluorides [1.20 eq. SASF hub, 1.00 eq. substituted glycine heating in Ac2O at 120 °C, 30 min]; 4g) 5-methyl-7-substituted-2,3-dihydro-1H-pyrrolizine-6-sulfonyl fluorides [1.20 eq. SASF hub, 1.00 eq. L-proline heating in Ac2O at 120 °C, 3 h]; 4h) 2,4,5-trisubstituted thiophene-3-sulfonyl fluoride [1.20 eq. SASF hub, 1.00 eq. 2-(benzoylthio)-2-substitutedarylacetic acid and 1.00 eq. TFAA in toluene at 120 °C, 16 h]; 4i) 1-benzyl-4-substituted-2,5-dihydro-1H-pyrrole-3-sulfonyl fluoride [1.00 eq. SASF hub, 1.10 eq. N-(methoxymethyl)-N-(trimethylsilylmethyl)benzylamine and 20.0 mol% TFA in CH2Cl2 at 0 °C, 30 min]; 4j) 1,3-disubstituted-5-oxo-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazole-2-sulfonyl fluorides [1.00 eq. SASF hub, 1.00 eq. azomethine imine heating in CDCl3 at 100 °C (μW), 30 min]; 4k) 2,3,5,7-tetrasubstituted-3,1a-dihydropyrido[1,2-d][1,4]diazepine-1-sulfonyl fluorides [1.00 eq. SASF hub, 1.20 eq. azomethine imine stirring in DCE at r.t., 4-40 h]; 4l) 3-substituted bicyclo[2.2.1]hepta-2,5-diene-2-sulfonyl fluoride and 1,3,4,5,6-pentasubstituted-7-oxabicyclo[2.2.1]hepta-2,5-diene-2-sulfonyl fluorides [1.00 eq. SASF hub, 1.00 eq. of diene in CH2Cl2 at r.t., 2-16 h] or [1.00 eq. SASF hub, 1.00 eq. of diene heating in DCE at reflux, 16 h].