Nozaki-Oshima reagent

Nozaki, Oshima, and Takai reported in 1978 that the reagent prepared from diio-domethane, zinc, and titanium(IV) chloride was effective for the methylenation of ketones [12]. In this procedure, a reagent was prepared by mixing diiodomethane (3.0 equiv.), zinc dust (9.0 equiv.), and titanium(IV) chloride (1.0 equiv.) in THF for 30 min at 25 °C. The ketone substrate (1.0 equiv.) was then added to the prepared reagent. Other metal halides were also examined (Scheme 5.5), but none of them gave better results than titanium) IV) chloride. 

Nozaki, H., Hiyama, T., Oshima, K., Takai, K. Highly selective synthesis with novel metallic reagents. ACS Symp. Ser. 1982, 185, 99-108. 

Matsubara, S., Tsuboniwa, N., Morizawa, Y., Oshima, K., Nozaki, H. Reformatskii type reaction with new aluminum reagents containing an aluminum-tin or aluminum-lead linkage. Bull. Chem. Soc. Jpn. 1984, 57, 3242-3246. 

Takai, K. Tagashira, M. Kuroda, T. Oshima, K. Utimoto, K. Nozaki, H., Reactions of Alkenylchromium Reagents Prepared from Alkenyl Trifluoromethanesulfonates (Triflates) with Chromium(II) Chloride under Nickel Catalysis. /. Am. Chem. Soc. 1986, 108,6048. 

Yasuda A, Tanaka S, Oshima K, Yamamoto H, Nozaki H (1974) Organoaluminum reagents of type R R NAlEt which allow regiospecific isomerization of epoxides to allylic alcohols. J Am Chem Soc 96 6513-6514... 

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