Benzeneselenenyl fluoride equivalent in situ generated with XeF2-(PhSe)2 in Ch2Cl2 for fluoroselenenylation of olefins

First Detection of a Selenenyl Fluoride ArSeF by NMR Spectroscopy: The Nature of Ar2Se2/XeF2 and ArSeSiMe3/XeF2 Reagents

“…But the Ph 2 Se 2 /XeF 2 reagent acts as an PhSe À F equivalent in addition reactions with alkenes and acetylenes. [7][8][9][10][11][12] PhSeÀF equivalents are also generated from PhSeÀEMe 3 (E = Si, Ge, Sn, Pb) and XeF 2 [13] or from PhSeOTf/ Et 3 N·3 HF. [14] Also the combinations PhSeÀBr/AgF/ultrasound, [15] PhSeÀCl/AgF/CH 3 CN, [16] N-phenylselenophthalimide (NPSP)/Py·9 HF, [17] or NPSP/Et 3 N·3 HF [18] and electro oxidation of Ph 2 Se 2 in Et 3 N·3 HF [19] act as PhSeÀF equivalents.…”

Trip2C6H3SeF: Das erste isolierte Selenenylfluorid

“…[2] Reagentien des Typs N-Phenylselenophthalimid/Et 3 N·3 HF, [3] Ph 2 Se 2 /XeF 2 , [4,5] PhSeEMe 3 / XeF 2 (E = Si, Ge, Sn, Pb) [5a, 6] und PhSeOTf/Et 3 N·3HF [7] fungieren als PhSeF-¾quivalente und kçnnen zur PhSeF-Addition an Olefine und Acetylene, hier über Selenireniumionen, [8] genutzt werden. Wir haben Arylselenmonofluoride, ArSeF, sowohl durch sterischen Schutz (Ar = 2,4,6-Tri-tertbutylphenyl = Supermesityl, Mes*) als auch durch intramolekulare Koordination mit Aminogruppen [9] (Ar = 2-Me 2 NCH 2 C 6 H 4 ) stabilisiert und deren Existenz erstmals NMR-spektroskopisch nachgewiesen.…”

“…[15,11] Zur Herstellung der REF (E = Se, Te) sollten neben den Dichalkogeniden, R 2 E 2 , auch die Trimethylsilyl-und Trimethylzinnchalkogenide, RESiMe 3 und RESnMe 3 , mit XeF 2 fluoriert werden. [4][5][6]10] Generell wurden die Reaktionsbedingungen durch Tieftemperatur-NMR-Experimente optimiert.…”

Functionalization of Organic Molecules by Xenon Fluorides

“…Diphenyl diselenide was transformed in CH 2 Cl 2 at −20 • C with xenon difluoride to benzeneselenyl fluoride, which further reacted with olefins preferentially by anti addition with Markovnikov-type regioselectivity 117 predominantly in a trans manner to give nonrearranged 2,3-selenofluorination adducts, corresponding to exo and endo attack, while in contrast phenylselenium trifluoride adds cis-exo, and the Wagner-Meerwein rearrangement products was also observed 118 (Scheme 50). SCHEME 50 2,5-Dihydrotellurophene-1,1-difluoride 119 was formed in the low-temperature reaction of 2,5-dihydrotellurophene with xenon difluoride.…”