Literature DB >> 11029202

Synthesis of 9-alkylidene-9H-fluorenes by a novel palladium-catalyzed rearrangement

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Abstract

In the presence of a palladium catalyst and NaOAc, aryl iodides react with 1-aryl-1-alkynes to afford 9-alkylidene-9H-fluorenes in good yields. This process appears to involve (1) oxidative addition of the aryl iodide to Pd(0), (2) alkyne insertion, (3) rearrangement of the resulting vinylic palladium intermediate to an arylpalladium species, and (4) aryl-aryl coupling with simultaneous regeneration of the Pd(0) catalyst.

Entities:  

Year:  2000        PMID： 11029202     DOI： 10.1021/ol000220h

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  5 in total

1.  Methoxy-directed aryl-to-aryl 1,3-rhodium migration.

Authors:  Jing Zhang; Jun-Feng Liu; Angel Ugrinov; Anthony F X Pillai; Zhong-Ming Sun; Pinjing Zhao
Journal:  J Am Chem Soc       Date:  2013-11-07       Impact factor: 15.419

2.  Synthesis of Fluorenes via the Palladium-Catalyzed 5-Exo-dig Annulation of o-Alkynyl Biaryls.

Authors:  Natalia Chernyak; Vladimir Gevorgyan
Journal:  Adv Synth Catal       Date:  2009-05-01       Impact factor: 5.837

3.  Iridium-catalyzed arylative cyclization of alkynones by 1,4-iridium migration.

Authors:  Benjamin M Partridge; Jorge Solana González; Hon Wai Lam
Journal:  Angew Chem Int Ed Engl       Date:  2014-05-19       Impact factor: 15.336

Review 4.  Modern Synthetic Methods for the Stereoselective Construction of 1,3-Dienes.

Authors:  Raquel G Soengas; Humberto Rodríguez-Solla
Journal:  Molecules       Date:  2021-01-06       Impact factor: 4.411

5.  Easy access to medium-sized lactones through metal carbene migratory insertion enabled 1,4-palladium shift.

Authors:  Yinghua Yu; Pushkin Chakraborty; Jinshuai Song; Lei Zhu; Chunsen Li; Xueliang Huang
Journal:  Nat Commun       Date:  2020-01-23       Impact factor: 14.919
  5 in total

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