Tin-free intermolecular addition of primary alkyls to imines via the dimethylzinc-air radical process

Organic Letters

Volumn 8, Issue 1, 2006, Pages 87-89

  Yamada, Ken Ichi ^a   Yamamoto, Yasutomo ^a   Maekawa, Masaru ^a   Akindele, Tito ^a   Umeki, Hiroyuki ^a   Tomioka, Kiyoshi ^a  

^a KYOTO UNIVERSITY   (Japan)

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Indexed keywords

EID: 30944437087     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol052563r     Document Type: Article

References (30)

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29. Attempts to obtain 10 in a one-pot reaction by heating the reaction mixture after the radical addition failed, probably due to low nucleophilicity of the zinc amide formed by the alkyl addition.
30. An alternative pathway of nonradical addition of dialkylzincs generated from alkyl iodides and dimethylzinc may be negligible because only a trace amount (< 1%) of methyl adduct was obtained in the reaction under argon atmosphere (Table 1, entry 13). Moreover, the iodine-zinc exchange between alkyl iodides and dimethylzinc is unlikely because the process would involve displacement of the less stable methyl radical by more stable primary or secondary alkyl radicals: Micouin, L.; Knochel, P. Synlett 1997, 327-328.