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Borostannylation of alkynes and enynes. Scope and limitations of the reaction and utility of the adducts.

ABSTRACT: The utility of the hetero-bismetallating reagent 1,3-dimethyl-2-trimethylstannyl-2-bora-1,3-diazacyclopentane (1) has not been fully realized because of the hydrolytic instability of the products derived from catalyzed vicinal syn-additions to alkynes. The isolation of a variety of such adducts derived from alkynes (and also from hitherto unreported additions to 1,3-enynes) as stable boron pinacolates is reported. Examples of the applications of resulting products in tandem cross-coupling reactions and as dienes in Diels-Alder reactions are illustrated.

SUBMITTER: Singidi RR

PROVIDER: S-EPMC2886519 | biostudies-literature | 2010 Jun

REPOSITORIES: biostudies-literature

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Borostannylation of alkynes and enynes. Scope and limitations of the reaction and utility of the adducts.

Singidi Ramakrishna Reddy RR RajanBabu T V TV

Organic letters 20100601 11

The utility of the hetero-bismetallating reagent 1,3-dimethyl-2-trimethylstannyl-2-bora-1,3-diazacyclopentane (1) has not been fully realized because of the hydrolytic instability of the products derived from catalyzed vicinal syn-additions to alkynes. The isolation of a variety of such adducts derived from alkynes (and also from hitherto unreported additions to 1,3-enynes) as stable boron pinacolates is reported. Examples of the applications of resulting products in tandem cross-coupling reacti ...[more]

PMID: 20459076

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