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Synthesis of Arylallenes by Palladium-Catalyzed Retro-Propargylation of Homopropargyl Alcohols
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Abstract
Treatment of tertiary homopropargyl alcohol with aryl halide under palladium catalysis provided arylallenes regioselectively. The reaction includes retro-propargylation, which proceeds in a concerted fashion via a cyclic transition state and transfers the stereochemistry of homopropargyl alcohols through C−C bond cleavage. The present method enables the use of homopropargyl alcohols as allenylmetal equivalents.
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This article has been cited by 4 ACS Journal articles (4 most recent appear below).
Synthesis of Conjugated Allenes through Copper-Catalyzed γ-Selective and Stereospecific Coupling between Propargylic Phosphates and Aryl- or Alkenylboronates
Mingyu Yang, Natsumi Yokokawa, Hirohisa Ohmiya, and Masaya SawamuraOrganic Letters2012 14 (3), 816-819Synthesis of Conjugated Allenes through Copper-Catalyzed γ-Selective and Stereospecific Coupling between Propargylic Phosphates and Aryl- or Alkenylboronates
Mingyu Yang, Natsumi Yokokawa, Hirohisa Ohmiya, and Masaya SawamuraOrganic Letters2012 14 (3), 816-819A Cu-catalyzed γ-selective coupling reaction between propargylic phosphates and aryl- or alkenylboronates afforded aryl- or alkenyl-conjugated allenes. The reaction showed excellent functional group compatibility in both the propargylic substrates and the ...
General Approach to Allenes through Copper-Catalyzed γ-Selective and Stereospecific Coupling between Propargylic Phosphates and Alkylboranes
Hirohisa Ohmiya, Umi Yokobori, Yusuke Makida, and Masaya SawamuraOrganic Letters2011 13 (23), 6312-6315General Approach to Allenes through Copper-Catalyzed γ-Selective and Stereospecific Coupling between Propargylic Phosphates and Alkylboranes
Hirohisa Ohmiya, Umi Yokobori, Yusuke Makida, and Masaya SawamuraOrganic Letters2011 13 (23), 6312-6315Copper-catalyzed γ-selective coupling between propargylic phosphates and alkylboron compounds (alkyl-9-BBN, prepared by hydroboration of alkenes with 9-BBN-H) affords multisubstituted allenes with various functional groups. The reaction of enantioenriched ...
Palladium-Catalyzed Annulation Reactions for Diastereoselective Cyclopentene Synthesis
Benjamin L. Kohn and Elizabeth R. JarvoOrganic Letters2011 Article ASAPPalladium-Catalyzed Annulation Reactions for Diastereoselective Cyclopentene Synthesis
Benjamin L. Kohn and Elizabeth R. JarvoOrganic Letters2011 Article ASAPPalladium-catalyzed annulation reactions of conjugate acceptors and allenyl boronic ester provide substituted cyclopentenes in high yields and, where applicable, diastereoselectivities. This method provides rapid assembly of building blocks for natural ...
Nickel-Catalyzed Arylative Ring-Opening of 3-Methylenecycloalkane-1,1-dicarboxylates
Yuto Sumida, Hideki Yorimitsu and Koichiro OshimaOrganic Letters2010 12 (10), 2254-2257Nickel-Catalyzed Arylative Ring-Opening of 3-Methylenecycloalkane-1,1-dicarboxylates
Yuto Sumida, Hideki Yorimitsu and Koichiro OshimaOrganic Letters2010 12 (10), 2254-2257An arylative ring-opening reaction of cyclic allylmalonates with arylzinc reagents under nickel catalysis has been developed. Upon the ring-opening sp3C−sp3C bond cleavage, the allylic moiety serves as an allylic electrophile to react with arylzinc ...
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History
- Published In Issue April 16, 2008
- Article ASAPMarch 19, 2008
- Received: February 08, 2008
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