An efficient synthesis of 2-(1-(E)-alkenyl)phenylphosphonates via Suzuki reaction of aryl nonaflates with (E)-1-alkenylboronates
In the presence of Pd(OAc)2, PPh3 and K2CO3, a series of 2-(1-(E)-alkenyl)phenylphosphonates were synthesized efficiently and stereoselectively via the Suzuki reaction of 2-phosphonylaryl nonaflates and (E)-1-alkenylboronic pinacol esters. •An efficient Suzuki reaction has been developed.•A series o...
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Veröffentlicht in: | Journal of fluorine chemistry 2013-07, Vol.151, p.58-62 |
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Format: | Artikel |
Sprache: | eng |
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Zusammenfassung: | In the presence of Pd(OAc)2, PPh3 and K2CO3, a series of 2-(1-(E)-alkenyl)phenylphosphonates were synthesized efficiently and stereoselectively via the Suzuki reaction of 2-phosphonylaryl nonaflates and (E)-1-alkenylboronic pinacol esters.
•An efficient Suzuki reaction has been developed.•A series of 2-(1-(E)-alkenyl)phenylphosphonates were synthesized.•The reactions are quite general.•The reactions proceed in good yields.
An efficient and general Suzuki coupling reaction between 2-phosphonylaryl nonaflates and (E)-1-alkenylboronic pinacol esters using Pd(OAc)2/PPh3 as catalysts, K2CO3 as base and DMF as solvent has been developed. This strategy allows for convenient synthesis of twelve 2-(1-(E)-alkenyl)phenylphosphonates in good to excellent yields, most of which are not readily available by the previously reported Heck reaction of the same aryl nonaflates and terminal alkenes. |
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ISSN: | 0022-1139 1873-3328 |
DOI: | 10.1016/j.jfluchem.2013.03.015 |