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Synthesis of functionalized organotrifluoroborates via the 1,3-dipolar cycloaddition of azides.

ABSTRACT: [reaction: see text] We have successfully prepared potassium azidoalkyltrifluoroborates from the corresponding halogen compounds in 94-98% yields through a nucleophilic substitution reaction with NaN(3). In the presence of various alkynes and Cu(I) as a catalyst, these azidotrifluoroborates easily formed 1,4-disubstituted organo-[1,2,3]-triazol-1-yl-trifluoroborates in 85-98% yields. This method was then developed into a facile one-pot synthesis for the preparation of various organo-[1,2,3]-triazol-1-yl-trifluoroborates using haloalkyltrifluoroborates as the starting materials.

SUBMITTER: Molander GA

PROVIDER: S-EPMC2515368 | biostudies-literature | 2006 Jun

REPOSITORIES: biostudies-literature

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Synthesis of functionalized organotrifluoroborates via the 1,3-dipolar cycloaddition of azides.

Molander Gary A GA Ham Jungyeob J

Organic letters 20060601 13

[reaction: see text] We have successfully prepared potassium azidoalkyltrifluoroborates from the corresponding halogen compounds in 94-98% yields through a nucleophilic substitution reaction with NaN(3). In the presence of various alkynes and Cu(I) as a catalyst, these azidotrifluoroborates easily formed 1,4-disubstituted organo-[1,2,3]-triazol-1-yl-trifluoroborates in 85-98% yields. This method was then developed into a facile one-pot synthesis for the preparation of various organo-[1,2,3]-tria ...[more]

PMID: 16774252

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