title: Cyclopropanation/Carboboration Reactions of Enynes with B(C6F5)3.
abstract: Stoichiometric reaction of B(C6F5)3 with 1,6-enynes is shown to proceed via initial cyclopropanation and formal 1,1-carboboration. Depending on the substitution on the alkene moiety, subsequent ring-opening of the cyclopropane affords either cyclopentane or cyclohexane derivatives in which the C6F5 and B(C6F5)2 adopt a 1,4-positioning. Mechanistically, this transformation involves π-activation of the alkyne moiety, which triggers cyclopropanation, followed by carboboration. Both the cyclopropanation and subsequent ring-opening are shown to be stereospecific. Both cyclopropanation and 1,4-carboborated products were employed as Lewis acid components in frustrated Lewis pair activation of H2 and CO2.
authors.affiliation: Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg , Im Neuenheimer Feld 270, 69120 Heidelberg, Germany.
authors.forename: Max M
authors.initials: MM
authors.lastname: Hansmann
authors.affiliation: School of Chemistry, Cardiff University , Main Building, Cardiff, CF10 3AT, Cymru/Wales, U.K.
authors.forename: Rebecca L
authors.initials: RL
authors.lastname: Melen
authors.affiliation: Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg , Im Neuenheimer Feld 270, 69120 Heidelberg, Germany.
authors.forename: Matthias
authors.initials: M
authors.lastname: Rudolph
authors.affiliation: Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg , Im Neuenheimer Feld 270, 69120 Heidelberg, Germany.
authors.forename: Frank
authors.initials: F
authors.lastname: Rominger
authors.affiliation: Anorganisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg , Im Neuenheimer Feld 270, 69120 Heidelberg, Germany.
authors.forename: Hubert
authors.initials: H
authors.lastname: Wadepohl
authors.affiliation: Department of Chemistry, University of Toronto , 80 Saint George Street, Toronto, Ontario M5S 3H6, Canada.
authors.forename: Douglas W
authors.initials: DW
authors.lastname: Stephan
authors.affiliation: Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg , Im Neuenheimer Feld 270, 69120 Heidelberg, Germany.|Chemistry Department, Faculty of Science, King Abdulaziz University (KAU) , Jeddah 21589, Saudi Arabia.
authors.forename: A Stephen K
authors.initials: AS
authors.lastname: Hashmi