title: Metal-free intermolecular formal cycloadditions enable an orthogonal access to nitrogen heterocycles.
abstract: Nitrogen-containing heteroaromatic cores are ubiquitous building blocks in organic chemistry. Herein, we present a family of metal-free intermolecular formal cycloaddition reactions that enable highly selective and orthogonal access to isoquinolines and pyrimidines at will. Applications of the products are complemented by a density functional theory mechanistic analysis that pinpoints the crucial factors responsible for the selectivity observed, including stoichiometry and the nature of the heteroalkyne.
authors.affiliation: Institute of Organic Chemistry, University of Vienna, Währinger Strasse 38, 1090 Vienna, Austria.
authors.forename: Lan-Gui
authors.initials: LG
authors.lastname: Xie
authors.affiliation: Institute of Organic Chemistry, University of Vienna, Währinger Strasse 38, 1090 Vienna, Austria.
authors.forename: Supaporn
authors.initials: S
authors.lastname: Niyomchon
authors.affiliation: Institute of Theoretical Chemistry, University of Vienna, Währinger Strasse 17, 1090 Vienna, Austria.
authors.forename: Antonio J
authors.initials: AJ
authors.lastname: Mota
authors.affiliation: Institute of Theoretical Chemistry, University of Vienna, Währinger Strasse 17, 1090 Vienna, Austria.
authors.forename: Leticia
authors.initials: L
authors.lastname: González
authors.affiliation: Institute of Organic Chemistry, University of Vienna, Währinger Strasse 38, 1090 Vienna, Austria.
authors.forename: Nuno
authors.initials: N
authors.lastname: Maulide
mesh_terms: D002384:Catalysis; D003500:Cyclization; D061565:Cycloaddition Reaction; D007546:Isoquinolines / Q000138:chemical synthesis*; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry*; D011743:Pyrimidines / Q000737:chemistry*; D013237:Stereoisomerism; D013816:Thermodynamics
chemical_list: D007546:Isoquinolines; D011743:Pyrimidines; D009584:Nitrogen