Novel One-Pot Approach to Synthesis of Indanones through Sb(V)-Catalyzed Reaction of Phenylalkynes with Aldehydes

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Abstract

Catalytic SbF₅ and the use of EtOH as an additive efficiently converted a mixture of phenylalkynes and aldehydes to indanone compounds in one pot, and the reaction stereoselectively afforded the corresponding 2,3-disubstituted indanones as a single trans-isomer.

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This article has been cited by 12 ACS Journal articles (5 most recent appear below).

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  Synthesis of 1-Indanones from Benzoic Acids

  Yun-Sheng Huang, Jian-Qiang Liu, Lang-Jun Zhang, and He-Lin Lu
  Industrial & Engineering Chemistry Research2012 51 (3), 1105-1109

  • Synthesis of 1-Indanones from Benzoic Acids

    Yun-Sheng Huang, Jian-Qiang Liu, Lang-Jun Zhang, and He-Lin Lu
    Industrial & Engineering Chemistry Research2012 51 (3), 1105-1109

    An improved process for the preparation of 1-indanones from various benzoic acids is described. This process involves a Friedel–Crafts acylation between a substituted benzoyl chloride and ethylene, followed by an intramolecular Friedel–Crafts alkylation ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Stereoselective Palladium-Catalyzed α-Arylation of 3-Aryl-1-Indanones: An Asymmetric Synthesis of (+)-Pauciflorol F

  Bong Hyang Lee, Young Lok Choi, Seunghoon Shin, and Jung-Nyoung Heo
  The Journal of Organic Chemistry2011 76 (16), 6611-6618

  • Stereoselective Palladium-Catalyzed α-Arylation of 3-Aryl-1-Indanones: An Asymmetric Synthesis of (+)-Pauciflorol F

    Bong Hyang Lee, Young Lok Choi, Seunghoon Shin, and Jung-Nyoung Heo
    The Journal of Organic Chemistry2011 76 (16), 6611-6618

    Highly stereoselective, palladium-catalyzed α-arylation reactions of 3-aryl-1-indanones with aryl bromides are described. The use of sodium tert-butoxide as a base in this process is required to elevate the efficiencies and stereoselectivities of these ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Iron-Catalyzed Synthesis of Functionalized 2H-Chromenes via Intramolecular Alkyne−Carbonyl Metathesis

  Krishnendu Bera, Soumen Sarkar, Srijit Biswas, Sukhendu Maiti, and Umasish Jana
  The Journal of Organic Chemistry2011 76 (9), 3539-3544

  • Iron-Catalyzed Synthesis of Functionalized 2H-Chromenes via Intramolecular Alkyne−Carbonyl Metathesis

    Krishnendu Bera, Soumen Sarkar, Srijit Biswas, Sukhendu Maiti, and Umasish Jana
    The Journal of Organic Chemistry2011 76 (9), 3539-3544

    An iron-catalyzed intramolecular alkyne−aldehyde metathesis strategy of the alkynyl ether of salicylaldehyde derivatives has been developed which works under mild reaction conditions to produce the functionalized 2H-chromene derivatives. This protocol is ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  A Concise Synthesis of Paucifloral F and Related Indanone Analogues via Palladium-Catalyzed α-Arylation

  Yang Yang, Dean Philips, and Shifeng Pan
  The Journal of Organic Chemistry2011 76 (6), 1902-1905

  • A Concise Synthesis of Paucifloral F and Related Indanone Analogues via Palladium-Catalyzed α-Arylation

    Yang Yang, Dean Philips, and Shifeng Pan
    The Journal of Organic Chemistry2011 76 (6), 1902-1905

    A concise approach to synthesize paucifloral F was developed via a stereoselective palladium-catalyzed α-arylation reaction. The approach has also been applied in the synthesis of indanone analogues of Paucifloral F.

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Direct Synthesis of 1-Indanones via Pd-Catalyzed Olefination and Ethylene Glycol-Promoted Aldol-Type Annulation Cascade

  Jiwu Ruan, Jonathan A. Iggo, and Jianliang Xiao
  Organic Letters2011 13 (2), 268-271

  • Direct Synthesis of 1-Indanones via Pd-Catalyzed Olefination and Ethylene Glycol-Promoted Aldol-Type Annulation Cascade

    Jiwu Ruan, Jonathan A. Iggo, and Jianliang Xiao
    Organic Letters2011 13 (2), 268-271

    A wide range of multisubstituted 1-indanones of potential pharmaceutical use were synthesized in a one-pot fashion in moderate to excellent yields via palladium catalysis in ethylene glycol. The Heck reaction first installs an enol functionality on the ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links

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