Efficient synthesis of functionalized organozinc compounds by the direct insertion of zinc into organic iodides and bromides

…, V Malakhov, A Gavryushin, P Knochel

Index: Krasovskiy, Arkady; Malakhov, Vladimir; Gavryushin, Andrei; Knochel, Paul Angewandte Chemie - International Edition, 2006 , vol. 45, # 36 p. 6040 - 6044

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Citation Number: 302

Abstract

yield for ortho-trifluoromethylphenyl iodide (2a) and no insertion occurs with ethyl 4- iodobenzoate (3a; 708C, 24 h, conversion< 5%). The organozinc iodides 2b and 3b react cleanly with electrophiles such as tetramethylthiuram disulfide [8] and allyl bromide to afford the corresponding products 2c and 3c in yields of 91 and 94%, respectively (Scheme 1). 4- Anisylzinc iodide (4a) can be prepared in 93% yield by the insertion of Zn in the presence ...