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Photochemical reactions of a diamidocarbene: cyclopropanation of bromonaphthalene, addition to pyridine, and activation of sp³ C-H bonds.

ABSTRACT: We report unprecedented photochemistry for the diamidocarbene 1. Described within are the double cyclopropanation of 1-bromonaphthalene, the double addition to pyridine, and remarkably, the insertion into the unactivated sp³ C-H bonds of cyclohexane, tetramethylsilane, and n-pentane to give compounds 2-6, respectively. All compounds have been fully characterized, and the solid state structure of 4 was obtained using single crystal electron diffraction.

SUBMITTER: Perera TA

PROVIDER: S-EPMC10370591 | biostudies-literature | 2023 Jul

REPOSITORIES: biostudies-literature

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Photochemical reactions of a diamidocarbene: cyclopropanation of bromonaphthalene, addition to pyridine, and activation of sp3 C-H bonds.

Perera Tharushi A TA Taylor William V WV Gildner M Brenton MB Reinheimer Eric W EW Ito Sho S Nelson Anna A Yost Shane R SR Hudnall Todd W TW

Chemical science 20230510 29

We report unprecedented photochemistry for the diamidocarbene 1. Described within are the double cyclopropanation of 1-bromonaphthalene, the double addition to pyridine, and remarkably, the insertion into the unactivated sp3 C-H bonds of cyclohexane, tetramethylsilane, and n-pentane to give compounds 2-6, respectively. All compounds have been fully characterized, and the solid state structure of 4 was obtained using single crystal electron diffraction. ...[more]

PMID: 37502328

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