Acridine adds secondary phosphine chalcogenides HP(X)R (X = O, S, Se; R = Ar, ArAlk) under catalyst-free conditions at 70-75 °C (both in the presence and absence of the electron-deficient acetylenes) to give 9-chalcogenophosphoryl-9,10-dihydroacridines in 61-94% yields. This contrasts with pyridines, which under similar conditions undergo an SAr reaction, wherein electron-deficient acetylenes play the role of oxidants. For acridine, the SAr step has been accomplished by the oxidation of the intermediate 9-phosphoryl-9,10-dihydroacridines (X = O) with chloranil.
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| http://dx.doi.org/10.1021/acs.orglett.8b03061 | DOI Listing |
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