Selective Deprotection of Me3Si-/Ph2P(O)-protected Arylalkynes: Methyl Grignard Reagent-promoted Dephosphorylation of Ph2P(O)-protected Alkynes

• Lifen Peng

  Department of Applied Chemistry, Okayama University of Science

• Feng Xu

  Department of Applied Chemistry, Okayama University of Science

• Kenta Shinohara

  Department of Applied Chemistry, Okayama University of Science

• Akihiro Orita

  Department of Applied Chemistry, Okayama University of Science

• Junzo Otera

  Department of Applied Chemistry, Okayama University of Science

Abstract

A Ph2P(O)-protected alkyne underwent dephosphorylation by treatment with MeMgBr in THF with Me3Si-protection untouched. The dephosphorylation followed by a transition-metal-catalyzed coupling of the resulting terminal alkyne with aryl halides was carried out in a one-pot manner to afford the desired coupling product. Selective deprotection of Me3Si-/Ph2P(O)-protected alkynes enabled facile syntheses of expanded π-systems such as cyclic phenyleneethynylenes and unsymmetrically substituted ditriazol.

Journal

• Chemistry Letters

  Chemistry Letters 43 (10), 1610-1612, 2014-07-03

  Oxford University Press (OUP)

Keywords

• General Chemistry

Details

• CRID: 1360002219105573632
• NII Article ID: 130004693828
• DOI: 10.1246/cl.140579
• ISSN: 13480715
• ISSN: 03667022
• Web Site: https://academic.oup.com/chemlett/article-pdf/43/10/1610/55644069/cl.140579.pdf
• Data Source:
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