title: Iterative Reductive Aromatization/Ring-Closing Metathesis Strategy toward the Synthesis of Strained Aromatic Belts.
abstract: The construction of all sp(2)-hybridized molecular belts has been an ongoing challenge in the chemistry community for decades. Despite numerous attempts, these double-stranded macrocycles remain outstanding synthetic challenges. Prior approaches have relied on late-state oxidations and/or acid-catalyzed processes that have been incapable of accessing the envisaged targets. Herein, we describe the development of an iterative reductive aromatization/ring-closing metathesis approach. Successful syntheses of nanohoop targets containing benzo[k]tetraphene and dibenzo[c,m]pentaphene moieties not only provide proof of principle that aromatic belts can be derived by this new strategy but also represent some of the largest aromatic belt fragments reported to date.
authors.affiliation: Department of Chemistry & Biochemistry and Material Science Institute, University of Oregon , Eugene, Oregon 97403, United States.
authors.forename: Matthew R
authors.initials: MR
authors.lastname: Golder
authors.affiliation: Department of Chemistry & Biochemistry and Material Science Institute, University of Oregon , Eugene, Oregon 97403, United States.
authors.forename: Curtis E
authors.initials: CE
authors.lastname: Colwell
authors.affiliation: Department of Chemical & Environmental Engineering and Materials Science & Engineering Program, University of California-Riverside , Riverside, California 92521, United States.
authors.forename: Bryan M
authors.initials: BM
authors.lastname: Wong
authors.affiliation: CAMCOR - Center for Advanced Materials Characterization in Oregon, University of Oregon , Eugene, Oregon 97403, United States.
authors.forename: Lev N
authors.initials: LN
authors.lastname: Zakharov
authors.affiliation: Department of Chemistry, Boston University , Boston, Massachusetts 02215, United States.
authors.forename: Jingxin
authors.initials: J
authors.lastname: Zhen
authors.affiliation: Department of Chemistry & Biochemistry and Material Science Institute, University of Oregon , Eugene, Oregon 97403, United States.
authors.forename: Ramesh
authors.initials: R
authors.lastname: Jasti
mesh_terms: D018360:Crystallography, X-Ray; D003500:Cyclization; D004563:Electrochemistry; D010084:Oxidation-Reduction