Alkynyliodonium tetrafluoroborates synthesis

So far, this method has been employed for the synthesis of (1) (Z)-(jS-sulfonylvinyl)-iodonium tetrafluoroborates from alkynyliodonium tetrafluoroborates with sulfinic acids in methanol (equation 46)32,84, (2) (Z )-(/ -azidovinyl)iodonium tetrafluoroborates from alkynyliodonium tetrafluoroborates with Me3SiN3, H20 (i.e. HN3) in dichloromethane (equation 110)102 and (3) (Z )-/ -bromo- and (jS-chlorovinyl)iodonium halides from alkynyliodonium tetrafluoroborates with lithium halides in acetic acid or with HX in methanol (equation 111 and 112)103. 

The alkynylation of phosphorus nucleophiles has been less investigated (Scheme 7). Ochiai and co-workers first demonstrated in 1987 that the alkynylation of triphenyl-phosphine was possible with alkynyliodonium tetrafluoroborate salts under light irradiation (Scheme 7, A) [69]. The reaction most probably involves radical intermediates. In 1992, Stang and Critell showed that light irradiation was not needed if alkynyliodonium triflates were used [70]. Later, this methodology could be extended to other triaryl- or alkyl phosphines [71, 72]. In 1990, Koser and Lodaya also reported the synthesis of alkynylphosphonates by the Arbusov reaction of alkynyliodonium tosylates with trialkyl phosphites (Scheme 7, B) [73]. Alternatively, the same compotmds can be obtained by the reaction of alkynyliodonium tosylates with sodium phosphonate salts [74]. 

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