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Reductive Dimerization of Macrocycles Activated by BBr₃.

ABSTRACT: A macrocyclic motif composed of carbazole and pyridine subunits linked by a carbonyl bridge (C═O) forms a skeleton with a peripheral reactivity that leads to a pinacol-like coupling activated by BBr₃, eventually entrapping a substantially elongated C-C bond. Slightly modified conditions lead to the efficient transformation of the C═O unit to a CH₂ linker that, after exposure to air, gives a dimeric molecule with multiple bonds between two macrocyclic units, as documented in spectroscopy and X-ray analysis.

SUBMITTER: Kijewska M

PROVIDER: S-EPMC8155568 | biostudies-literature | 2021 May

REPOSITORIES: biostudies-literature

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Reductive Dimerization of Macrocycles Activated by BBr3.

Kijewska Monika M Siczek Miłosz M Pawlicki Miłosz M

Organic letters 20210415 9

A macrocyclic motif composed of carbazole and pyridine subunits linked by a carbonyl bridge (C═O) forms a skeleton with a peripheral reactivity that leads to a pinacol-like coupling activated by BBr3, eventually entrapping a substantially elongated C-C bond. Slightly modified conditions lead to the efficient transformation of the C═O unit to a CH2 linker that, after exposure to air, gives a dimeric molecule with multiple bonds between two macrocyclic units, as documented in ...[more]

PMID: 33856224

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