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

abstract

• Herein, we report a synthesis of medicinally relevant -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.

authors

• Michaudel, Quentin

published proceedings

• Org Lett

altmetric score

• 21.8

author list (cited authors)

• Sousa E Silva, F. C., Doktor, K., & Michaudel, Q.

citation count

• 9

complete list of authors

• Sousa E Silva, Felipe Cesar||Doktor, Katarzyna||Michaudel, Quentin

publication date

• July 2021

publisher

• American Chemical Society (ACS)  Publisher

published in

• Organic Letters  Journal

keywords

• Click Chemistry
• Fluorides
• Molecular Structure
• Sulfonamides
• Sulfonic Acids
• Sulfur

PubMed Central ID

• 34151557

Digital Object Identifier (DOI)

• 10.1021/acs.orglett.1c01907

start page

• 5271

end page

• 5276

volume

• 23

issue

• 13

URL

• http://dx.doi.org/10.1021/acs.orglett.1c01907