title: Borylative Radical Cyclizations of Benzo[3,4]cyclodec-3-ene-1,5-diynes and N-Heterocyclic Carbene-Boranes.
abstract: Borylative radical cyclization of benzo[3,4]cyclodec-3-ene-1,5-diynes to provide 5-borylated 6,7,8,9-tetrahydrobenzo[a]azulenes has been developed. The experimental results suggest that the reaction proceeds by a radical chain mechanism, in which di-tert-butyl hyponitrite (TBHN) works as a good radical initiator to form boryl radicals from N-heterocyclic carbene-boranes (NHC-boranes). The present reaction is a rare model that illustrates addition of boryl radicals to alkynes.
authors.affiliation: School of Pharmaceutical Sciences, Institute of Medical, Pharmaceutical and Health Sciences, Kanazawa University, Kakuma-machi, Kanazawa, 920-1192, Japan.
authors.forename: Takashi
authors.initials: T
authors.lastname: Watanabe
authors.affiliation: Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa, 920-1192, Japan.
authors.forename: Daisuke
authors.initials: D
authors.lastname: Hirose
authors.affiliation: Department of Chemistry, University of Pittsburgh, Pittsburgh, PA, 15260, USA.
authors.forename: Dennis P
authors.initials: DP
authors.lastname: Curran
authors.affiliation: School of Pharmaceutical Sciences, Institute of Medical, Pharmaceutical and Health Sciences, Kanazawa University, Kakuma-machi, Kanazawa, 920-1192, Japan.
authors.forename: Tsuyoshi
authors.identifier: http://orcid.org/0000-0002-4945-480X
authors.initials: T
authors.lastname: Taniguchi
keywords: alkynes; boron; main group chemistry; radical reactions; strained molecules