Zinc-iron couple induced conjugate addition of alkyl halide derived radicals to activated olefins

Pierre Blanchard; Adilson D. Da Silva; Mohammed S. El Kortbi; Jean Louis Fourrey; Malka Robert-Gero

doi:10.1021/jo00075a066

Zinc-iron couple induced conjugate addition of alkyl halide derived radicals to activated olefins

The Journal of Organic Chemistry ◽

10.1021/jo00075a066 ◽

1993 ◽

Vol 58 (23) ◽

pp. 6517-6519 ◽

Cited By ~ 19

Author(s):

Pierre Blanchard ◽

Adilson D. Da Silva ◽

Mohammed S. El Kortbi ◽

Jean Louis Fourrey ◽

Malka Robert-Gero

Keyword(s):

Alkyl Halide ◽

Conjugate Addition ◽

Activated Olefins

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ChemInform Abstract: Zinc-Iron Couple Induced Conjugate Addition of Alkyl Halide Derived Radicals to Activated Olefins.

ChemInform ◽

10.1002/chin.199410254 ◽

2010 ◽

Vol 25 (10) ◽

pp. no-no

Author(s):

P. BLANCHARD ◽

A. D. DA SILVA ◽

M. S. EL KORTBI ◽

J.-L. FOURREY ◽

M. ROBERT-GERO

Keyword(s):

Alkyl Halide ◽

Conjugate Addition ◽

Activated Olefins

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Co-Catalyzed Conjugate Addition of Aryl Halides to Activated Olefins

Synfacts ◽

10.1055/s-2006-949311 ◽

2006 ◽

Vol 2006 (10) ◽

pp. 1048-1048

Author(s):

C. Gosmini ◽

M. Amatore ◽

J. Périchon

Keyword(s):

Conjugate Addition ◽

Aryl Halides ◽

Activated Olefins

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Carbon-Carbon Bond Formation

Organic Synthesis ◽

10.1093/oso/9780199965724.003.0025 ◽

2013 ◽

Author(s):

Douglass F. Taber

Keyword(s):

Alkyl Halide ◽

Bond Formation ◽

Conjugate Addition ◽

Phenyl Isocyanate ◽

Ni Catalyst ◽

Reductive Coupling ◽

Carbon Carbon Bond ◽

University Of Technology ◽

Osaka Prefecture ◽

The University

Akiya Ogawa of Osaka Prefecture University found (Tetrahedron Lett. 2010, 51, 6580) that the Sm-mediated reductive coupling of a halide 1 with CO2 to give the carboxylic acid 2 was strongly promoted by visible light. Gregory C. Fu of MIT designed (Angew. Chem. Int. Ed. 2010, 49, 6676) a Ni catalyst for the coupling of a primary borane 4 with a secondary alkyl halide 3. James P. Morken of Boston College devised (Org. Lett. 2010, 12, 3760) conditions for the carbonylative conjugate addition of a dialkyl zinc to an enone 6 to give the 1,4-dicarbonyl product 7. Louis Fensterbank of the Institut Parisien de Chimie Moléculaire developed (Angew. Chem. Int. Ed. 2010, 49, 8721; not illustrated) a protocol for the conjugate addition of alkyl boranes to enones. Hyunik Shin of LG Life Science, Daejeon, and Sang-gi Lee of Ewha Womans University showed (Tetrahedron Lett. 2010, 51, 6893) that the intermediate from Blaise homologation of a nitrile 8 was a powerful nucleophile, smoothly opening an epoxide 10 to deliver 11. Sébastien Reymond and Janine Cossy of ESPCI ParisTech found (J. Org. Chem. 2010, 75, 5151) that FeCl3 smoothly catalyzed the coupling of an alkenyl Grignard 13 with the primary iodide 12. The Ti-mediated coupling of an alkyne 16 with an allylic alkoxide 15 (J. Am. Chem. Soc. 2010, 132, 9576) developed by Glenn C. Micalizio of Scripps/Florida was the key step in the total synthesis (J. Am. Chem. Soc. 2010, 132, 11422) of lehualide B. Huanfeng Jiang of the South China University of Technology observed (Chem. Commun. 2010, 46, 8049) that KI added to a bromoalkyne 18 to give the dihalide 19 with high geometric control. Haruhiko Fuwa of Tohoku University improved (Org. Lett. 2010, 12, 5354) the selective hydroiodination of a methyl alkyne 20 to 21. Takuya Kurahashi and Seijiro Matsubara of Kyoto University devised (Chem. Commun. 2010, 46, 8055) the Ni-catalyzed three-component coupling of an alkyne 22, methyl acrylate 23, and phenyl isocyanate to give the doubly homologated lactam 24. Patrick H. Toy of the University of Hong Kong showed (Synlett 2010, 1997; Org. Lett. 2010, 12, 4996 for a polymer with covalently attached base) that resin-bound triphenylphosphine participated efficiently in the Wittig coupling of 26 with an aldehyde 25.

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