Iterative Reductive Aromatization/Ring-Closing Metathesis Strategy toward the Synthesis of Strained Aromatic Belts.

Autor:	Golder MR; Department of Chemistry & Biochemistry and Material Science Institute, University of Oregon , Eugene, Oregon 97403, United States., Colwell CE; Department of Chemistry & Biochemistry and Material Science Institute, University of Oregon , Eugene, Oregon 97403, United States., Wong BM; Department of Chemical & Environmental Engineering and Materials Science & Engineering Program, University of California-Riverside , Riverside, California 92521, United States., Zakharov LN; CAMCOR - Center for Advanced Materials Characterization in Oregon, University of Oregon , Eugene, Oregon 97403, United States., Zhen J; Department of Chemistry, Boston University , Boston, Massachusetts 02215, United States., Jasti R; Department of Chemistry & Biochemistry and Material Science Institute, University of Oregon , Eugene, Oregon 97403, United States.
Jazyk:	angličtina
Zdroj:	Journal of the American Chemical Society [J Am Chem Soc] 2016 May 25; Vol. 138 (20), pp. 6577-82. Date of Electronic Publication: 2016 May 12.
DOI:	10.1021/jacs.6b02240
Abstrakt:	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.
Databáze:	MEDLINE
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