Journal Article Contiguous radical pivaloyloxymethylation–directed C(sp3)–H iodination of N-tosyl cycloalkanecarbaldimine

Fujii, Shintaro  ,  Nakano, Mayu  ,  Yamaoka, Yousuke  ,  Takasu, Kiyosei  ,  Yamada, Ken-ichi  ,  Tomioka, Kiyoshi

56 ( 23 )  , pp.3086 - 3089 , 2015-06 , Elsevier Ltd.
Available online 27 November 2014
A reaction of N-tosyl cycloalkanecarbaldimines with iodomethyl pivalate was initiated by triethylborane to give pivaloyloxymethylated products bearing 3-iodocycloalkyl groups. Radical addition of pivaloyloxymethyl to imines generates aminyl radicals, which then regioselectively cleave Csingle bondH bonds at the 3-position of the cycloalkane moieties. The resulting carbon-centered radicals are trapped with iodine. DFT calculations rationalized stereo- and regioselectivity.

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