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C(sp³)-C(sp³) coupling of non-activated alkyl-iodides with electron-deficient alkenes via visible-light/silane-mediated alkyl-radical formation.

ABSTRACT: Here, we present a remarkably mild and general initiation protocol for alkyl-radical generation from non-activated alkyl-iodides. An interaction between a silane and an alkyl iodide is excited by irradiation with visible light to trigger carbon-iodide bond homolysis and form the alkyl radical. We show how this method can be developed into an operationally simple and general Giese addition reaction that can tolerate a range of sensitive functionalities not normally explored in established approaches to this strategically important transformation. The new method requires no photocatalyst or other additives and uses only commerical tris(trimethylsilyl)silane and visible light to effectively combine a broad range of alkyl halides with activated alkenes to form C(sp³)-C(sp³) bonds embedded within complex frameworks.

SUBMITTER: Mistry S

PROVIDER: S-EPMC9667957 | biostudies-literature | 2022 Nov

REPOSITORIES: biostudies-literature

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C(sp3)-C(sp3) coupling of non-activated alkyl-iodides with electron-deficient alkenes via visible-light/silane-mediated alkyl-radical formation.

Mistry Sanesh S Kumar Roopender R Lister Andrew A Gaunt Matthew J MJ

Chemical science 20221028 44

Here, we present a remarkably mild and general initiation protocol for alkyl-radical generation from non-activated alkyl-iodides. An interaction between a silane and an alkyl iodide is excited by irradiation with visible light to trigger carbon-iodide bond homolysis and form the alkyl radical. We show how this method can be developed into an operationally simple and general Giese addition reaction that can tolerate a range of sensitive functionalities not normally explored in established approac ...[more]

PMID: 36425511

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