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

Felipe Cesar Sousa e Silva | Zendy; Katarzyna Doktor | Zendy; Quentin Michaudel | Zendy

Open Access

Modular 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 , sequence (biology) , combinatorial chemistry , organic chemistry , nitrogen , 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.

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