|Title:||Contiguous radical pivaloyloxymethylation–directed C(sp3)–H iodination of N-tosyl cycloalkanecarbaldimine|
Takasu, Kiyosei https://orcid.org/0000-0002-1798-7919 (unconfirmed)
|Author's alias:||山田, 健一|
Csingle bondH functionalization
Aminyl radical generation
Csingle bondC bond formation
|Journal title:||Tetrahedron Letters|
|Abstract:||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.|
|Description:||Available online 27 November 2014|
|Rights:||© 2014. This manuscript version is made available under the CC-BY-NC-ND 4.0 license http://creativecommons.org/licenses/by-nc-nd/4.0/|
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|Appears in Collections:||Journal Articles|
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