Iron-Catalyzed Kharasch-Type Reaction Between Grignard Reagents and Allylic Phosphates.Highly SN2 Selective Cross-Coupling Process

Akira Yanagisawa; Nobuyoshi Nomura; Hisashi Yamamoto

doi:10.1055/s-1991-20783

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Synlett 1991; 1991(7): 513-514
DOI: 10.1055/s-1991-20783

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Iron-Catalyzed Kharasch-Type Reaction Between Grignard Reagents and Allylic Phosphates.Highly S_N2 Selective Cross-Coupling Process

Akira Yanagisawa^* , Nobuyoshi Nomura, Hisashi Yamamoto

^*Department of Applied Chemistry, Nagoya University, Chikusa, Nagoya 464-01, Japan

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Publication Date:
07 March 2002 (online)

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Treatment of primary allylic phosphates in tetrahydrofuran with Grignard reagents in the presence of an iron catalyst gave cross-coupling products with high S_N2 selectivity. Among several phosphate leaving groups, diphenylphosphate ester showed the highest regioselectivity.