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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 26, 1996 - Issue 19
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Original Articles

Efficient Syntheses of 4-Iodopyridine and of 4-Pyridylboronic Acid Pinacol Ester

Pages 3543-3547 | Received 15 Apr 1996, Published online: 21 Aug 2006

References

  • Miyaura , N. and Suzuki , A. 1995 . Chem. Rev. , 95 : 2457 For a leading reference about boron derivatives in cross-coupling reactions and their preparations, see
  • Murray , A. and Langham , W. H. 1952 . J. Am. Chem. Soc. , 74 : 6289
  • Gaus , P. L. , Haim , A. and Johnson , F. 1977 . J. Org. Chem. , 42 : 564
  • Albers , W. A. , Canters , G. W. and Reedijk , J. 1995 . Tetrahedron , 51 : 3895
  • Furukawa , N. , Shibutani , T. and Fujihira , H. 1987 . Tetrahedron Lett. , 28 : 5847
  • Brandsma , L. and Verkruijsse , H. 1987 . Preparative Polar Organometallic Chemistry 1 , 175 Berlin : Springer .
  • van Zoest , W. J. and den Hertog , H. J. 1974 . Recl. Trav. Chim. Pays-Bas , 93 : 166
  • Gergely , E. and Iredale , T. 1953 . J. Chem. Soc. , : 3226
  • Roe , A and Hawkins , G. F. 1947 . J. Am. Chem. Soc. , 69 : 2443
  • Roe , A. and Little , W. 1955 . J. Org. Chem. , 20 : 1577
  • Oh-e , T. , Miyaura , N. and Suzuki , A. 1993 . J. Org. Chem. , 58 : 2201
  • Fischer , F. C. and Havinga , E. 1965 . Recl. Trav. Chim. Pays-Bas , 84 : 439
  • Thompson , W. J. , Jones , J. H. , Lyle , P. A. and Thies , J. E. 1988 . J. Org. Chem. , 53 : 2052
  • Mitchell , M. B. and Wallbank , J. P. 1991 . Tetrahedron Lett. , 32 : 2273 Use of 4-pyridylboronic acid has been scarcely reported for cross-coupling reactions. See
  • Fujita , M. , Oka , H. and Ogura , K. 1995 . Tetrahedron Lett. , 36 : 5247 See
  • No further purification is required for the next step. Analytical sample of iodopyridine (off-white, sublimable solid) is obtained by passing a CH2Cl2 solution of the crude product through an alumina pad and evaporation. It should be stored at +4°C and rapidly used
  • Hot filtration may be necessary to remove some brown impurity

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