期刊
ORGANOMETALLICS
卷 33, 期 8, 页码 2099-2108出版社
AMER CHEMICAL SOC
DOI: 10.1021/om5002827
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资金
- Fonds der Chemischen Industrie
- Fonds der Chemischen Industrie for Chemiefonds
For the first time the anionic phospho-Fries rearrangement has been successfully applied in ferrocene chemistry, giving access to 1,2-P,O-substituted ferrocenes. The 1,3 (O -> C)-migration occurs at ferrocenyl phosphates, thiophosphates, phosphite borane adducts, and phosphinates by treatment with a base such as lithium diisopropylamide at low temperature, whereas the highest yields were obtained starting from diethylferrocenyl phosphate. Complete reduction of the phosphonate to a primary phosphine and subsequent Stelzer P,C cross coupling allowed the synthesis of Fe(eta(5)-C5H3-2-OMe-PPh2)(eta(5)-C5H5) (1). The qualification of 1 as a supporting ligand in palladium-catalyzed Suzuki-Miyaura C,C couplings has been proven by the synthesis of sterically congested tri-ortho-substituted biaryls under mild reaction conditions in good to excellent yields.
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