Quinones, stannylated

The synthesis of the second Stille coupling partner 34 was efficiently achieved in three steps. First, 2-bromojuglone (36) [28] was protected as its methoxymethyl ether (46, Scheme 3.7). The quinone was reduced using sodium thiosulfate, and the resulting hydroquinone was protected with methoxymethyl chloride to afford the arene 47. Finally, stannylation using tetrakis-(triphenylphosphine)palladium and hexabutylditin [29] afforded the cross-coupling partner 34 in high yield. 

Stannyl groups attached to quinones can be displaced by aryl, heteryl and other groups, as shown in reactions 32286 and 67314. 

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