Modular Synthesis of Alkenyl Sulfamates and β-Ketosulfonamides via Sulfur(VI) Fluoride Exchange (SuFEx) Click Chemistry and Photomediated 1,3-Rearrangement
Felipe Cesar Sousa e Silva, Katarzyna Doktor, Quentin Michaudel
Abstract
Herein, we report a synthesis of medicinally relevant β-ketosulfonamides via a photomediated 1,3-rearrangement of alkenyl sulfamates. This protocol tolerates a wide array of sensitive functional groups including alkenes, alkynes, and nitrogen-based heterocycles. Additionally, this work provides a general approach toward alkenyl sulfamates via a two-step Sulfur(VI) Fluoride Exchange (SuFEx) sequence capitalizing on SO2F2 as a linchpin to efficiently couple readily available ketones and amines without a large excess of either partner.
Topics & Concepts
ChemistrySulfurFluorideSequence (biology)Combinatorial chemistryOrganic chemistryNitrogenInorganic chemistryBiochemistrySulfur-Based Synthesis TechniquesSynthesis and Catalytic ReactionsRadical Photochemical Reactions