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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 24, 1994 - Issue 6
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Original Articles

Palladium-Catalyzed Coupling of Stannyl Allenes With Aryl Iodides

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Pages 789-797 | Received 26 Jul 1993, Published online: 16 Feb 2007

References

  • Alexakis Marek , A. II , Mangeney , P. and Normant , J. F. 1990 . J. Am. Chem. Soc. , 112 : 8042 – 8047 . For leading references, see:
  • Stille , J. K. 1986 . Angew. Chem. Int. Ed. Engl. , 25 : 508 – 524 . For palladium-catalyzed coupling reactions of organotin reagents with aryl iodides, see:
  • Mitchell , T. N. 1992 . Synthesis , : 803 – 815 .
  • Graaf , W. , Boersma , J. , van Koten , G. and Elsevier , C. J. 1989 . J. Organomet. Chem. , 378 : 115 – 124 . and references cited therein. For palladium-catalyzed couplings of highly reactive allenyl metals (allenyl zinc or magnesium reagents) prepared in situ, see:
  • Schwab , J. M and Lin , D. C. T. 1985 . J. Am. Chem. Soc. , 107 : 6046 – 6052 . and references cited therein;For examples of other allenyl metals used in synthesis, see: lithium:
  • Landor , S. R. , Demetriou , B. , Evans , R. J. , Grzoskowiak , R. and Davey , P. 1972 . J. Chem. Soc., Perkin Trans. II , : 1995 – 1998 . magnesium:
  • Konoike , T. and Araki , Y. 1992 . Tetrahedron Lett. , 33 : 5093 – 5096 . For an alternative allene synthesis involving radical hydrostannylation of propargyl alcohols, see:
  • Keinan , E. and Peretz , M. 1983 . J. Org. Chem. , 48 : 5302 – 5309 . Palladium-catalyzed allylation of stannyl allenes with allyl acetates as coupling partners has been investigated, however in these reactions the major products are the isomeric propargylated compounds:
  • Mandai , T. , Kunitomi , H. , Higashi , K. , Kawada , M. and Tsuji , J. 1991 . Synlett , : 697 – 698 . Coupling of allenyl palladium species formed in situ from propargyl carbonates or acetates has been carried out with: sodium malonates:
  • Bouyssi , D. , Gore , J. , Balme , G. , Louis , D. and Wallach , J. 1993 . Tetrahedron Lett. , 34 : 3129 – 3130 . vinyl potassium species:
  • Tsuji , J. , Sugiura , T. and Minami , I. 1987 . Synthesis , : 603 – 606 . hydride from ammonium formate:
  • Brandsma , L. and Verkruijsse , H. D. 1981 . Synthesis of Acetylenes, Allenes and Cumulenes , 223 New York : Elsevier Scientific Publishing Company .
  • Tadema , G. , Everhardus , R. H. , Westmijze , H. and Vermeer , P. 1978 . Tetrahedron Lett. , : 3935 – 3936 . In the case where R = Ph, both the tosylate and the mesylate were unstable (being both propargylic and benzylic); however the sulfinate is an isolable compound:
  • Marshall , J. A. and Wang , X. 1992 . J. Org. Chem. , 57 : 1242 – 1252 . and references cited therein.
  • In some cases the very non-polar stannyl allene product was inseparable from tin byproducts (either Bu3SnH or Bu3Sn-SnBu3). In these cases the allene content was estimated by 1H-NMR, and the mixture was submitted to the palladium coupling reaction.
  • Ukai , T. , Kawazura , H. , Ishii , Y. , Bonnet , J. J. and Ibers , J. A. 1974 . Organomet. Chem. , 65 : 253 – 266 . The chloroform used in the recrystallization of Pd(dba)2 was washed with water, dried over magnesium sulfate, and then distilled over calcium hydride to remove the ethanol stabilizer. Amorphous material obtained in this manner was found to be a far superior catalyst to highly The Pd2dba3. CHCl3 was prepared following the procedure of crystalline samples.
  • All allene coupling products have been previously described (see experimental section for individual references)
  • Scott , W. J. , Crisp , G. T. and Stille , J. K. 1984 . J. Am. Chem. Soc. , 106 : 4630 – 4632 .
  • Farina , V. and Krishnan , B. 1991 . J. Am. Chem. Soc. , 113 : 9585 – 9595 .
  • Stille , J. K. and Simpson , J. H. 1987 . J. Am. Chem. Soc. , 109 : 2138 – 2152 .
  • Buckle , M. J. C. and Fleming , I. 1993 . Tetrahedron Lett. , 34 : 2383 – 2386 . The copper-mediated synthesis of optically active allenes from propargyl alcohol derivatives has been demonstrated using Grignard reagents:
  • Elsevier , C. J. and Vermeer , P. 1989 . J. Org. Chem. , 54 : 3726 – 3730 .
  • Mannschreck , A. , Munninger , W. , Burgemeister Gore , T. and Cazes , J. B. 1986 . Tetrahedron , 42 : 399 – 408 . see reference 1. c.
  • Ruitenberg , K. , Westmijze , H. , Meijer , J. , Elsevier , C. J. and Vermeer , P. 1983 . J. Organometal. Chem. , 241 : 417 – 422 . The use of stannyl cuprates has also been demonstrated:
  • See reference 15. a.
  • Burton , D. J. , Hartgraves , G. A. and Hsu , J. 1990 . Tetrahedron Lett. , 31 : 3699 – 3702 .
  • see reference 17.
  • see reference 7.
  • Douglass , I. B. and Norton , R. V. 1968 . J. Org. Chem. , 33 : 2104 – 2106 .
  • Ueno , Y. and Okawara , M. 1979 . J. Am. Chem. Soc. , 101 : 1893 – 1894 .
  • Haruta , J. , Nishi , K. , Kikuchi , S. , Matsuda , S. , Tamura , Y. and Kita , Y. 1989 . Chem. Pharm. Bull. , 37 : 2338 – 2343 .
  • This compound was only marginally stable, and was submitted to the palladium coupling conditions immediately following chromatographic purification. The corresponding 3-phenyl-1-(tripheny/stannyl)-1,2-propadiene has been prepared: see reference 15.e.
  • see reference 7, page 164.
  • Okuyama , T. , Izawa , K. and Fueno , T. 1973 . J. Am. Chem. Soc. , 95 : 6749 – 6752 . see reference 15.c. b.
  • see reference 25.b.
  • Vermeer , P. , Meijer , J. and Brandsma , L. 1975 . Recl. Trav. Chim. Pays-Bas , 94 : 112 – 114 .

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