Open AccessModular Synthesis of Alkenyl Sulfamates and β-Ketosulfonamides via Sulfur(VI) Fluoride Exchange (SuFEx) Click Chemistry and Photomediated 1,3-Rearrangement
Author(s) -
Felipe Cesar Sousa E Silva,
Katarzyna Doktor,
Quentin Michaudel
Publication year - 2021
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.1c01907
Subject(s) - chemistry , sulfur , fluoride , organic chemistry , nitrogen , sequence (biology) , combinatorial chemistry , inorganic chemistry , biochemistry
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 SO 2 F 2 as a linchpin to efficiently couple readily available ketones and amines without a large excess of either partner.