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Suzuki-Miyaura cross-coupling of potassium alkoxyethyltrifluoroborates: access to aryl/heteroarylethyloxy motifs.

ABSTRACT: The introduction of an alkoxyethyl moiety onto aromatic substructures has remained a long-standing challenge for synthetic organic chemists. The main reasons are the inherent instability of alkoxyethylmetallic species and the lack of general procedures to access them. A new method utilizing a cross-coupling strategy based on the exceptional properties of organotrifluoroborates has been developed, and the method allows an easy and efficient installation of this unit on a broad range of aryl and heteroaryl bromides.

SUBMITTER: Fleury-Bregeot N 

PROVIDER: S-EPMC3514869 | biostudies-literature | 2012 Nov

REPOSITORIES: biostudies-literature

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Suzuki-Miyaura cross-coupling of potassium alkoxyethyltrifluoroborates: access to aryl/heteroarylethyloxy motifs.

Fleury-Brégeot Nicolas N   Presset Marc M   Beaumard Floriane F   Colombel Virginie V   Oehlrich Daniel D   Rombouts Frederik F   Molander Gary A GA  

The Journal of organic chemistry 20121106 22

The introduction of an alkoxyethyl moiety onto aromatic substructures has remained a long-standing challenge for synthetic organic chemists. The main reasons are the inherent instability of alkoxyethylmetallic species and the lack of general procedures to access them. A new method utilizing a cross-coupling strategy based on the exceptional properties of organotrifluoroborates has been developed, and the method allows an easy and efficient installation of this unit on a broad range of aryl and h  ...[more]

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