• Title/Summary/Keyword: Ortho-functionalization

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Transition Metal-Catalyzed Ortho-Functionalization in Organic Synthesis

  • Park, Young-Jun;Jun, Chul-ho
    • Bulletin of the Korean Chemical Society
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    • v.26 no.6
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    • pp.871-877
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    • 2005
  • Recent progress in the filed of transition-metal mediated C-H bond activation has had a great influence on organic synthesis. Among such transition-metal catalyzed reactions, ortho-functionalization via the chelationassisted strategy has been paid great attentions as one of the powerful methodologies for converting aromatic compounds into ones that are more functionalized at the exclusively ortho-position. In this context, various transition metal-catalyzed ortho-functionalizations such as alkylation, alkenylation, silylation and carbonylation are described briefly and their prospects are suggested.

Facile Syntheses and Multi-orthofunctionalizations of Tertiary Benzamides

  • Paek, Kyung-Soo;Kim, Kyung-Mo;Kim, You-Seung
    • Bulletin of the Korean Chemical Society
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    • v.14 no.6
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    • pp.732-739
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    • 1993
  • Good yields were usually obtained in Pd(O)-catalyzed Suzuki aryl-aryl coupling reaction, even when both coupling partners had an ortho tertiary benzamide functional group. The direct ortho functionalization of oligomeric tertiary benzamides at Snieckus condition is dependent on the chain length. Tertiary benzamide 1 can be o,o-dilithiated only by metal-halogen exchange of the 2,6-dihalo-compound. Bis-tertiary benzamide 9 can be o,o'-dilithiated with excess(4.1 equivalents) s-butyllithium/TMEDA as the lithiating agent. Tris-tertiary benzamide 21 is hard to o,o"-difunctionalize due to steric interactions among the tertiary benzamide functional groups, and due to steric interactions between these functional groups and others (if present) on the termini of the terphenyl unit.