29788-12-3Relevant academic research and scientific papers
Cationic gold(I) π-complexes of terminal alkynes and their conversion to dinuclear σ,π-acetylide complexes
Brown, Timothy J.,Widenhoefer, Ross A.
, p. 6003 - 6009 (2011)
Treatment of a suspension of (IPr)AuCl [IPr = 1,3-bis(2,6- diisopropylphenyl)imidazol-2-ylidene] and AgSbF6 with terminal arylacetylenes led to the formation of thermally unstable gold π-alkyne complexes of the form [(IPr)Au(η 2-HC≡ CAr)]+SbF 6 - in ≥86 ± 5% yield, which were characterized by spectroscopy without isolation. Warming these complexes to 0 °C led to C(sp)-H bond cleavage and formation of dinuclear gold(I) σ,π-acetylide complexes of the form {[(IPr)Au]2(η 1,η 2-C≡ CAr)}+SbF6 -, three of which were isolated in 99% yield and one of which was characterized by X-ray crystallography. 1H NMR analysis of the conversion of gold π-arylacetylene complexes to σ,π-acetylide complexes established protonation of free arylacetylene, indicating the generation of a strong Bronsted acid under reaction conditions.
Modular Synthesis of Alkenyl Sulfamates and β-Ketosulfonamides via Sulfur(VI) Fluoride Exchange (SuFEx) Click Chemistry and Photomediated 1,3-Rearrangement
Sousa E Silva, Felipe Cesar,Doktor, Katarzyna,Michaudel, Quentin
supporting information, p. 5271 - 5276 (2021/07/20)
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.
