Journal of Synthetic Organic Chemistry, Japan
Online ISSN : 1883-6526
Print ISSN : 0037-9980
ISSN-L : 0037-9980
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Volume 71, Issue 4
Displaying 1-10 of 10 articles from this issue
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Preface
Reviews and Accounts
  • Copper-catalyzed Conjugate Addition of Organoboronic Acids and Esters to Electron-Deficient Alkynes
    Yoshihiko Yamamoto
    2013 Volume 71 Issue 4 Pages 296-306
    Published: April 01, 2013
    Released on J-STAGE: May 09, 2013
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.71.296
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    In the presence of catalytic amounts of copper salts, CuOAc or Cu(OAc)2, the reaction of arylboronic acids with electron-deficient alkynes proceeded in MeOH at ambient temperature to afford hydroarylation products with high chemo- and stereoselectivity. This method of synthesizing tri-substituted alkenes was further applied to the synthesis of biologically interesting molecules such as butenolides/pentenolides, 4-arylcoumarins, 3,3-diarylacrylonitriles, and 3-arylindole-2-carboxylates. Among them, the tandem hydroarylation/lactonization leading to 4-arylcoumarins is particularly fascinating as seven natural products were synthesized by the combination of three alkynoates and four boronic acids.
    The copper-catalyzed conjugate addition was further extended to that of allylboronates as organoboron reagents. Thus, the copper-catalyzed conjugate allylation of various electron-deficient alkynes was achieved and the derivatization of the introduced allyl moiety was also investigated.
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  • Novel Synthesis and Luminescent Properties of Silicon-bridged Biaryls
    Masaki Shimizu
    2013 Volume 71 Issue 4 Pages 307-318
    Published: April 01, 2013
    Released on J-STAGE: May 09, 2013
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.71.307
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    This account reviews our research on the development of palladium-catalyzed synthesis of silicon-bridged biaryls to which growing interest has been paid in materials science and on the design and characterization of the silicon-bridged biaryls that can be accessible via the palladium-catalyzed reactions we developed.
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  • Chiral Azolium Salts for Cu-catalyzed Asymmetric Conjugate Addition Reactions
    Satoshi Sakaguchi
    2013 Volume 71 Issue 4 Pages 319-329
    Published: April 01, 2013
    Released on J-STAGE: May 09, 2013
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.71.319
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    The Cu-catalyzed 1,4-addition of organometallic reagents to α,β-unsaturated compounds is a powerful method for the efficient construction of carbon-carbon bonds. In the past decade, catalytic asymmetric conjugate addition reactions with high enantioselectivities have been successfully achieved by using a variety of chiral ligands. Among the growing number of the chiral ligands, N-heterocyclic carbenes (NHCs) have been recognized as useful ligands. One of the most attractive features that make NHCs a very interesting class of ligands is the easy access to their ligand precursors (mostly azolium salts). The azolium salts are very easy to functionalize often by simple reactions that allows the design of a wide variety of NHC ligands and the rapid elaboration of NHC ligand libraries. In this review article, the Cu-catalyzed asymmetric conjugate addition reactions by employing easy accessible and highly tunable functionalized azolium salts are summarized.
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  • Syntheses and Properties of Functional π-Conjugated Molecules Based on Characteristics of Boron
    Tomohiro Agou, Takayuki Kawashima
    2013 Volume 71 Issue 4 Pages 330-340
    Published: April 01, 2013
    Released on J-STAGE: May 09, 2013
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.71.330
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    From the viewpoint of the improvement of organic optoelectronic devices, including organic electroluminescence devices, organic solar cells, and organic field effect transistors, development of novel π-conjugated molecules with unique structures and properties should be of great importance. In the course of our study on functional π-systems by taking advantage of characteristics of main group elements, we have synthesized dibenzoheteraborin-based hetero-π-conjugated molecules. Rigid and planar π-backbones of the dibenzoheteraborin derivatives have been shown to enhance synergetic interactions between the main group elements. In this paper, syntheses and properties of the dibenzoheteraborin derivatives involving various main group elements, such as nitrogen, oxygen, phosphorus, sulfur, and selenium, are described.
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  • Synthesis of Heteroaromatic Compounds by Newly Extended Pummerer Reactions
    Hideki Yorimitsu
    2013 Volume 71 Issue 4 Pages 341-354
    Published: April 01, 2013
    Released on J-STAGE: May 09, 2013
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.71.341
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    Ketene dithioacetal monoxides (KDMs) bring out a variety of latent intriguing reactivity upon treatment with triflic anhydride. The extended Pummerer reactions of KDMs provide reliable accesses to heteroaromatic compounds including (benzo) furan, (benzo) thiophene, and pyrroles. Trifluoromethyl-substituted KDMs are useful building blocks to prepare α-trifluoromethyl carbonyl compounds and 3-trifluoromethyl heteroaromatic compounds. A newly uncovered interrupted Pummerer reaction/[3,3]sigmatropic rearrangement cascade is the key that realizes most of the transformations in this paper. The last part of this paper describes the first example of metal-catalyzed Pummerer reaction where sulfoxides are directly activated by the catalyst.
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Review de Debut
  • Meta Selective C-H Bond Functionalization
    Hiroaki Gotoh
    2013 Volume 71 Issue 4 Pages 355-356
    Published: April 01, 2013
    Released on J-STAGE: May 09, 2013
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.71.355
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    Substituted arenes are important building blocks for many natural products, medicines and materials. Functionalization of unactivated carbon-hydrogen (C-H) bonds is an efficient strategy for preparation of these compounds without substrate prefunctionalization. The traditional C-H activation methods utilized proximate heteroatom directing groups that direct selective cleavage of ortho C-H bonds and formconformationally rigid metallacycles. However, recent advances in the field have enabled meta-selective C-H functionalizations.
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