title: 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.
authors.affiliation: Department of Chemistry, The Ohio State University, 100 West 18th Avenue, Columbus, Ohio 43210, USA.
authors.forename: Ramakrishna Reddy
authors.initials: RR
authors.lastname: Singidi
authors.forename: T V
authors.initials: TV
authors.lastname: RajanBabu
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D001896:Boron Compounds / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D015394:Molecular Structure; D014298:Trimethyltin Compounds / Q000737:chemistry*
chemical_list: C551414:1,3-dimethyl-2-trimethylstannyl-2-bora-1,3-diazacyclopentane; D000475:Alkenes; D000480:Alkynes; D001896:Boron Compounds; D014298:Trimethyltin Compounds
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