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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 27, 1997 - Issue 4
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Original Articles

Palladium-Catalyzed Homocoupling of Organostannanes

, &
Pages 641-646 | Received 23 Jul 1996, Published online: 20 Aug 2006

References and Notes

  • (a) For reviews see: (a) Mitchell T. N. Synthesis 1992 803 815
  • Stille , J. K. 1986 . Angew. Chem. Int. Ed. Engl. , 25 : 508 – 524 .
  • Kanemoto , S. , Matsubara , S. , Oshima , K. , Utimoto , K. and Nozaki , H. 1987 . Chem. Lett. , : 5 – 6 .
  • Shinya , Y. , Kariya , M. and Kikukawa , K. 1994 . 10th International Conference on Organic Synthesis . December 11–16 1994 , Bangalore, India. poster number, P-THU-90. As mild oxidizing agent, ClCH2COR (R = Me) was used
  • Liebeskind , L. S. and Riesinger , S.W. 1991 . Tetrahedron Lett. , 32 : 5681 – 5682 .
  • Boons , G-J. , Entwistle , D. A. , Ley , S. V. and Woods , M. 1993 . Tetrahedron Lett. , 34 : 5649 – 5652 . Homocoupling of alkenylstannanes was also accomplished after conversion to alkenyllithium with PdCl2(CH3CN)2 and CuCl2. See
  • Tolstikov , G. A. , Miftakhov , M. S. , Danilova , N. A. , Velder , Ya. L. and Spirikhin , L. Y. 1989 . Synthesis , : 633 – 634 .
  • In the Stille coupling reaction of olefinic stannanes considerable amounts of stannane homocoupling were encountered though mechanistically unexplainable. See, Friesen R. W. Sturino C. F. J. Org. Chem. 1990 55 2572 2574
  • Dubois , E. and Beau , J. M. 1990 . Tetrahedron Lett. , 31 : 5165 – 5168 .
  • In the Stille coupling, the use of triphenylarsine as ligand accelerates the rates. See, Farina V. Krishinan B. J. Am. Chem. Soc. 1991 113 9585 9595
  • Presumably, 1, 2-dichloroethane regenerates Pd(II) by oxidation of Pd(0) in catalytic cycle if double transmetallation followed by reductive elimination is assumed. For the use of 1, 2-dichloroethane as Pd(0) reoxidant, see, Ait-Mohand S. Henin F. Muzart J. Tetrahedron Lett. 1995 36 2473 2476
  • Larock , R. C. and Bernhardt , J. C. 1977 . J. Org. Chem. , 42 : 1680 – 1684 .

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