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A Widely Applicable Synthetic Approach to Alk‐1‐yn‐1‐yl(polyfluoroorganyl)‐iodonium Salts [(RC≡C)(R′)I][BF 4 ]
Author(s) -
Frohn HermannJosef,
Bardin Vadim V.
Publication year - 2008
Publication title -
zeitschrift für anorganische und allgemeine chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.354
H-Index - 66
eISSN - 1521-3749
pISSN - 0044-2313
DOI - 10.1002/zaac.200700319
Subject(s) - difluoride , chemistry , electrophile , aryl , medicinal chemistry , stereochemistry , alkyl , organic chemistry , catalysis
The reaction of alkynyldifluoroboranes RC≡CBF 2 (R = (CH 3 ) 3 C, CF 3 , (CF 3 ) 2 CF) with organyliodine difluoride R′IF 2 bearing electron‐withdrawing polyfluoroorganyl groups R′ = C 6 F 5 , (CF 3 ) 2 CFCF=CF, C 4 F 9 , and CF 3 CH 2 leads to the corresponding alkynyl(organyl)iodonium salts [(RC≡C)(R′)I][BF 4 ]. This approach uses a widely applicable method as demonstrated for a representative series of polyfluorinated aryl‐, alkenyl‐, and alkyliodine difluorides. Generally, these syntheses proceed with good yields and deliver pure iodonium salts. The distinct electrophilic nature of their [(RC≡C)(R′)I] + cations is deduced from multinuclear magnetic resonance data. Within the series of new iodonium salts [CF 3 C≡C(C 4 F 9 )I][BF 4 ] is an intrinsic unstable one and decomposed forming CF 3 C≡CI and C 4 F 10 .