Modular Synthesis of Alkenyl Sulfamates and β‑Ketosulfonamides via Sulfur(VI) Fluoride Exchange (SuFEx) Click Chemistry and Photomediated 1,3-Rearrangement

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 ge...

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Bibliographic Details
Published in:Organic letters 2021-07, Vol.23 (13), p.5271-5276
Main Authors: Sousa e Silva, Felipe Cesar, Doktor, Katarzyna, Michaudel, Quentin
Format: Article
Language:English
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c01907