title: Substrate-Controlled Product Divergence: Conversion of CO2 into Heterocyclic Products.
abstract: Substituted epoxy alcohols and amines allow substrate-controlled conversion of CO2 into a wide range of heterocyclic structures through different mechanistic manifolds. This new approach results in an unusual scope of CO2-derived products by initial activation of CO2 through either the amine or alcohol unit, thus providing nucleophiles for intramolecular epoxy ring opening under mild reaction conditions. Control experiments support the crucial role of the amine/alcohol fragment in this process with the nucleophile-assisted ring-opening step following an SN i pathway, and a 5-exo-tet cyclization, thus leading to heterocyclic scaffolds.
authors.affiliation: Institute of Chemical Research of Catalonia (ICIQ), the Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007, Tarragona, Spain.
authors.forename: Jeroen
authors.initials: J
authors.lastname: Rintjema
authors.affiliation: Institute of Chemical Research of Catalonia (ICIQ), the Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007, Tarragona, Spain.
authors.forename: Roel
authors.initials: R
authors.lastname: Epping
authors.affiliation: Institute of Chemical Research of Catalonia (ICIQ), the Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007, Tarragona, Spain.
authors.forename: Giulia
authors.initials: G
authors.lastname: Fiorani
authors.affiliation: Institute of Chemical Research of Catalonia (ICIQ), the Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007, Tarragona, Spain.
authors.forename: Eddy
authors.initials: E
authors.lastname: Martín
authors.affiliation: Institute of Chemical Research of Catalonia (ICIQ), the Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007, Tarragona, Spain.
authors.forename: Eduardo C
authors.initials: EC
authors.lastname: Escudero-Adán
authors.affiliation: Institute of Chemical Research of Catalonia (ICIQ), the Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007, Tarragona, Spain. akleij@iciq.es.|Catalan Institute of Research and Advanced Studies (ICREA), Pg. Lluís Companys 23, 08010, Barcelona, Spain. akleij@iciq.es.
authors.forename: Arjan W
authors.initials: AW
authors.lastname: Kleij
keywords: Lewis acids; carbon dioxide fixation; heterocycles; homogeneous catalysis; small ring systems