Article

Synthesis of benzo[c] and naphtho[c]heterocycle diesters and dinitriles via homoelongation.

128 Academia Road, 2nd Sec., Nankang Taipei, Taiwan ROC.
The Journal of Organic Chemistry (Impact Factor: 4.56). 11/2009; 74(23):9180-7. DOI: 10.1021/jo901754w
Source: PubMed

ABSTRACT Syntheses of benzo[c] and naphtho[c]heterocycle diesters and dinitriles were achieved via our newly developed iterative elongation protocol. The photophysical and electrochemical properties of these conjugated systems are explored.

0 Bookmarks
 · 
40 Views
  • [Show abstract] [Hide abstract]
    ABSTRACT: Over the past few years, isoindoles have found wide application in materials science. Isoindole containing BODIPY dyes are highly fluorescent materials and have been extensively used in various fields of science. Phthalocyanines, metal containing cyclic tetramers of isoindole, form coordination complexes with most elements of the periodic table. These complexes are intensely coloured and are used as pigments and dyes. However, isoindoles are relatively unstable 10π-heteroaromatic systems and few synthetic methods provide these compounds in good yields. This tutorial review will give an overview of the reported synthetic methods towards isoindoles and related heteroaromatic systems over a time span of approximately 10 years (2000 to current), including the applications where they have been reported. The importance of the field will be illustrated and factors influencing product stability will be discussed.
    Chemical Society Reviews 07/2012; 41(17):5626-40. · 24.89 Impact Factor
  • [Show abstract] [Hide abstract]
    ABSTRACT: Previously, we developed an iterative elongation methodology to synthesize acene esters, nitriles, and imides. The strategy uses the concept of bidirectional synthesis, and we can now make a series of electron deficient anthracene, tetracene, and pentacene derivatives via the bidirectional iterative elongation protocol. Central units, used to initiate the bidirectional elongation, were synthesized by employing a double anionic Fries rearrangement as the key step. The photophysical and electrochemical properties of these novel electron acceptors are investigated and interpreted based on the electron withdrawing power of the substitutions. An excited state charge transfer was proposed for one compound to account for its peculiar fluorescent behavior.
    Organic & Biomolecular Chemistry 04/2011; 9(12):4507-17. · 3.57 Impact Factor
  • [Show abstract] [Hide abstract]
    ABSTRACT: 3-Formylfuran derivatives are core structures of a variety of bioactive natural products. However, procedures for their preparation are still rare and generally inefficient in terms of atom economy: These methods require multiple steps or harsh reaction conditions and show selectivity problems. An efficient gold(I)-catalyzed cascade reaction that leads to 3-formylfurans from easily accessible starting materials is now described. A wide variety of 3-formylfurans were obtained from the corresponding symmetric and unsymmetric 1,4-diyn-3-ols in the presence of an N-oxide in good to excellent yields. Isotope-labeling experiments as well as DFT calculations support a mechanism in which, after an initial oxygen transfer, a 1,2-alkynyl migration is favored over a hydride shift; a cyclization ensues to afford the desired functionalized furan core.
    Angewandte Chemie International Edition 02/2014; · 11.34 Impact Factor