Strategies for the synthesis of bi- and triarylic materials starting from commercially available phenols

A series of arylstannanes have been synthesized, through an SRN1 mechanism, in good to excellent yields (74%–99%) by the photostimulated reaction of trimethyl stannyl ion with substrates supporting different nucleofugal groups. The arylstannanes thus obtained were suitable intermediates for Stille cross-coupling reactions leading to asymmetric bi- and triaryl compounds in acceptable global yields. An attractive feature of this route is that simple commercially available benzenediols, chloro- and methoxy phenols might be useful starting substrates, leading the latter to higher global yields of products in fewer steps. The strategies proposed open a broad synthetic tool.

Graphical abstractThe photostimulated reaction of Me3SnNa with aryl substrates supporting different nucleofugal groups yielded the corresponding arylstannanes (74–99%) which, through Stille cross-coupling reactions, led to asymmetric bi- and triaryls in acceptable global yields. Commercially available benzenediols, chloro- and methoxy phenols might be useful starting substrates.Figure optionsDownload full-size imageDownload as PowerPoint slide