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A homologation approach to the synthesis of difluorinated cycloalkynes.


ABSTRACT: Difluorinated cyclooctynes are important reagents for labeling azido-biomolecules through copper-free click chemistry. Here, a safe, scalable synthesis of a difluorinated cyclooctyne is reported, which involves a key homologation/ring-expansion reaction. Sequential ring expansions were also employed to synthesize and study a novel difluorinated cyclononyne.

SUBMITTER: Sletten EM 

PROVIDER: S-EPMC3993865 | biostudies-other | 2014 Mar

REPOSITORIES: biostudies-other

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A homologation approach to the synthesis of difluorinated cycloalkynes.

Sletten Ellen M EM   de Almeida Gabriela G   Bertozzi Carolyn R CR  

Organic letters 20140303 6


Difluorinated cyclooctynes are important reagents for labeling azido-biomolecules through copper-free click chemistry. Here, a safe, scalable synthesis of a difluorinated cyclooctyne is reported, which involves a key homologation/ring-expansion reaction. Sequential ring expansions were also employed to synthesize and study a novel difluorinated cyclononyne. ...[more]

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