Triarylantimony dicarboxylates as pseudo-halides for palladium-catalyzed cross-coupling reaction with arylboronic acids and triarylbismuthanes without any base

The reaction of triarylantimony diacetates (6) with organoboron reagents (9) in the presence of Pd(PPh3)4 led to the formation of cross-coupling products, biaryls (10, 12 and 14–17), in moderate to excellent yields under mild conditions without any base. Similar reaction of 6 with triarylbismuthanes (18) also gave the corresponding cross-coupling products. Single crystal X-ray analysis of tri(p-tolyl)antimony diacetate (6b) and tris(p-trifluoromethylphenyl)antimony diacetate (6e) revealed the geometry of both central antimony atoms being intermediate between trigonal bipyramidal and pentagonal bipyramidal arrangement with intramolecular coordination between the antimony and two carbonyl oxygen atoms with cis orientation.

Graphical abstractThe reaction of triarylantimony diacetates with arylboronic acids and triarylbismuthane in the presence of Pd(PPh3)4 led to the formation of cross-coupling products, biaryls, under mild conditions without any base. Single crystal X-ray analysis of tri(p-tolyl)- and tris(p-trifluoromethylphenyl)-antimony diacetates revealed the presence of intramolecular coordination between the antimony and two carbonyl oxygen atoms with cis orientation.Figure optionsDownload full-size imageDownload as PowerPoint slide