The use of a modified Suzuki reaction for the synthesis of monoarylferrocenes
A modification of the Suzuki cross-coupling reaction proved to be a clean and useful method for the preparation of monosubstituted arylferrocenes. Iodoferrocene was reacted with a series of substituted arylboronic acids in the presence of sodium carbonate and palladium acetate in aqueous ethanol at...
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| Vydáno v: | Perkin transactions. 1 číslo 17; s. 2513 - 2523 |
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| Hlavní autoři: | , , , |
| Médium: | Journal Article |
| Jazyk: | angličtina |
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CAMBRIDGE
Royal Soc Chemistry
1999
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| ISSN: | 0300-922X |
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| Abstract | A modification of the Suzuki cross-coupling reaction proved to be a clean and useful method for the preparation of monosubstituted arylferrocenes. Iodoferrocene was reacted with a series of substituted arylboronic acids in the presence of sodium carbonate and palladium acetate in aqueous ethanol at room temperature to produce a range of substituted monoarylferrocenes. A systematic investigation undertaken to determine optimal reaction conditions indicated that scrupulous deoxygenation of the solvent is critical. The use of stronger bases such as barium hydroxide and potassium carbonate is favourable and gives rise to better yields of monoarylferrocenes. The reactions also proceed efficiently in aqueous DMF, broadening the scope of the reaction allowing efficient reactions with boronic acids that show low solubility in organic solvents. |
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| AbstractList | A modification of the Suzuki cross-coupling reaction proved to be a clean and useful method for the preparation of monosubstituted arylferrocenes. Iodoferrocene was reacted with a series of substituted arylboronic acids in the presence of sodium carbonate and palladium acetate in aqueous ethanol at room temperature to produce a range of substituted monoarylferrocenes. A systematic investigation undertaken to determine optimal reaction conditions indicated that scrupulous deoxygenation of the solvent is critical. The use of stronger bases such as barium hydroxide and potassium carbonate is favourable and gives rise to better yields of monoarylferrocenes. The reactions also proceed efficiently in aqueous DMF, broadening the scope of the reaction allowing efficient reactions with boronic acids that show low solubility in organic solvents. |
| Author | McCleland, CW Loubser, C Engelbrecht, P Imrie, C |
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| Keywords | HALOARENES PALLADIUM FERROCENE DERIVATIVES CRYSTAL-STRUCTURE BEHAVIOR ARYLBORONIC ACIDS |
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| References | WEINMAYR, V (WOS:A1955WB85800027) 1955; 77 ROSENBLUM, M (WOS:A19623077B00042) 1962; 84 GALYAMETDINOV YG (WOS:000082423200020.9) 1990 LEE, MT (WOS:A1985ADN1400019) 1985; 4 MIYAURA, N (WOS:A1981MF20600001) 1981; 11 NESMEYANOV AN (WOS:000082423200020.31) 1954; 99 NESMEYANOV AN (WOS:000082423200020.30) 1962; 147 TOMA S (WOS:000082423200020.42) 1976; 24 LITTLE, WF (WOS:A1960WT08500040) 1960; 25 FISH, RW (WOS:A19656341500077) 1965; 30 MASON, JG (WOS:A1960WB34300023) 1960; 82 POETSCH E (WOS:000082423200020.35) 1988; 2 GALYAMETDINOV, YG (WOS:A1994QE27600036) 1994; 43 IMRIE, C (WOS:A1994PJ67500068) 1994 PAUSON PL (WOS:000082423200020.33) 1990 RAUSCH, MD (WOS:A19616268B00106) 1961; 26 BROADHEAD, GD (WOS:A1955WK63500020) 1955 PAUSON, PL (WOS:A1954UB49700046) 1954; 76 GALYAMETDINOV, YG (WOS:A1990FU81700023) 1990; 39 CAMPI, EM (WOS:A1994PN86900040) 1994 GALYAMETDINOV YG (WOS:000082423200020.8) 1994 NESMEYANOV, AN (WOS:A19649736A00041) 1964; 154 BITTERWOLF, TE (WOS:A1977EC75100015) 1977; 141 GALYAMETDINOV YG (WOS:000082423200020.12) 1995 LITTLE, WF (WOS:A19643140B00022) 1964; 86 SONG, ZZ (WOS:A1994MT48800009) 1994; 59 MALTHETE, J (WOS:A1976CT89000001) 1976; 34 NESMEYANOV AN (WOS:000082423200020.32) 1954; 97 ROSENBLUM, M (WOS:A1959WB36800023) 1959; 81 ALLEN, FH (WOS:A1970F942200027) 1970 LITTLE, WF (WOS:A1964WZ10600009) 1964 RAUSCH, MD (WOS:A19622612B00039) 1962; 1 HANASAKI, T (WOS:A1993MN00800030) 1993; 237 COE, BJ (WOS:A1994MT39400015) 1994; 464 SOLLOTT, GP (WOS:A1969D340000085) 1969; 34 KORIDZE, AA (WOS:A1971K840600007) 1971; 32 MIYAURA, N (WOS:A1995TD89200007) 1995; 95 LOUBSER, C (WOS:A1993KH57000008) 1993; 5 BECKWITH, ALJ (WOS:A1992HR89900006) 1992; 45 IMRIE C (WOS:000082423200020.14) 1993 LORKOWSKI HJ (WOS:000082423200020.21) 1965; 27 WALLOW, TI (WOS:A1994PE44300056) 1994; 59 Loubser, C (WOS:A1997WN48100002) 1997 MorenoManas, M (WOS:A1996UD65300019) 1996; 61 |
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| Title | The use of a modified Suzuki reaction for the synthesis of monoarylferrocenes |
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