Efficient syntheses of 4-iodopyridine and of 4-pyridylboronic acid pinacol ester

Synthetic Communications

Volumn 26, Issue 19, 1996, Pages 3543-3547

  Coudret, Christophe ^a  

^a CEMES CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOBORON DERIVATIVE; PYRIDINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029839081     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919608003763     Document Type: Article

References (17)

1. For a leading reference about boron derivatives in cross-coupling reactions and their preparations, see Miyaura N., Suzuki A., Chem. Rev. 1995, 95, 2457.
2. Murray A., Langham W. H., J. Am. Chem. Soc. 1952, 74, 6289; Gaus P. L., Haim A., Johnson F., J. Org. Chem. 1977, 42, 564; Albers W. A., Canters G. W., Reedijk J., Tetrahedron 1995, 51, 3895.
3. Murray A., Langham W. H., J. Am. Chem. Soc. 1952, 74, 6289; Gaus P. L., Haim A., Johnson F., J. Org. Chem. 1977, 42, 564; Albers W. A., Canters G. W., Reedijk J., Tetrahedron 1995, 51, 3895.
4. Murray A., Langham W. H., J. Am. Chem. Soc. 1952, 74, 6289; Gaus P. L., Haim A., Johnson F., J. Org. Chem. 1977, 42, 564; Albers W. A., Canters G. W., Reedijk J., Tetrahedron 1995, 51, 3895.
5. Furukawa N., Shibutani T., Fujihira H., Tetrahedron Lett. 1987, 28, 5847.
6. Brandsma L., Verkruijsse H., Preparative Polar Organometallic Chemistry 1, Springer, Berlin, 1987, p 175.
7. van Zoest W. J., den Hertog H. J., Recl. Trav. Chim. Pays-Bas 1974, 93, 166.
8. Gergely E., Iredale T., J. Chem. Soc. 1953, 3226.
9. Roe A, Hawkins G. F., J. Am. Chem. Soc. 1947, 69, 2443.
10. Roe A., Little W., J. Org. Chem. 1955, 20, 1577.
11. Oh-e T., Miyaura N., Suzuki A., J. Org. Chem. 1993, 58, 2201.
12. Fischer F. C., Havinga E., Recl. Trav. Chim. Pays-Bas 1965, 84, 439.
13. Use of 4-pyridylboronic acid has been scarcely reported for cross-coupling reactions. See: Thompson W. J., Jones J. H., Lyle P. A., Thies J. E., J. Org. Chem. 1988, 53, 2052; Mitchell M. B., Wallbank J. P., Tetrahedron Lett. 1991, 32, 2273.
14. Use of 4-pyridylboronic acid has been scarcely reported for cross-coupling reactions. See: Thompson W. J., Jones J. H., Lyle P. A., Thies J. E., J. Org. Chem. 1988, 53, 2052; Mitchell M. B., Wallbank J. P., Tetrahedron Lett. 1991, 32, 2273.
15. See : Fujita M., Oka H., Ogura K., Tetrahedron Lett. 1995, 36, 5247.
16. 2 solution of the crude product through an alumina pad and evaporation. It should be stored at +4°C and rapidly used.
17. Hot filtration may be necessary to remove some brown impurity.