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Triarylantimony dicarboxylates as pseudo-halides for palladium-catalyzed cross-coupling reaction with arylboronic acids and triarylbismuthanes without any base |
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| Authors: | Weiwei Qin Shuji Yasuike Naoki Kakusawa Masatoshi Kawahata Jyoji Kurita |
| Affiliation: | a Faculty of Pharmaceutical Sciences, Hokuriku University, Kanagawa-machi, Kanazawa 920-1181, Japan b Organization for Frontier Research in Pharmaceutical Sciences, Hokuriku University, Kanagawa-machi, Kanazawa 920-1181, Japan c Faculty of Pharmaceutical Sciences at Kagawa Campus, Tokushima Bunri University, Shido, Sanuki 769-2193, Japan |
| Abstract: | 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. |
| Keywords: | Base-free Triarylantimony diacetate Aryl-aryl bond formation Pd-catalyzed cross-coupling Arylboronic acid Triarylbismuthane |
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