Literature DB >> 25133776

Silver-catalyzed domino hydroarylation/cycloisomerization reactions of ortho-alkynylbenzaldehydes: an entry to functionalized isochromene derivatives.

Gaëlle Mariaule1, Gregory Newsome, Patrick Y Toullec, Philippe Belmont, Véronique Michelet.   

Abstract

A Ag-catalyzed versatile and efficient access to 1H,1-arylisochromenes is reported. Starting from ortho-alkynylbenzaldehydes bearing various substitution patterns on the benzaldehyde and alkynyl units, the use of silver triflate (10 mol %) allowed a domino hydroarylation/cycloisomerization reaction process, leading to aryl-functionalized 1H-isochromene (>10 compounds, 80-98% yields). Notably, the reaction conditions were also compatible with benzaldehydes bearing an aliphatic-substituted alkynyl moiety with modest to good yields (34-88%, 10 compounds).

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Year:  2014        PMID: 25133776     DOI: 10.1021/ol5021256

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


  5 in total

1.  Rapid synthesis of 3-amino-1H-isochromene from ortho-ynamidyl het(aryl) aldehyde derivatives.

Authors:  Loïc Habert; Iryna Diachenko; Isabelle Gillaizeau
Journal:  RSC Adv       Date:  2020-03-10       Impact factor: 4.036

2.  Ruthenium(0)-Catalyzed [4+2] Cycloaddition of Acetylenic Aldehydes with α-Ketols: Convergent Construction of Angucycline Ring Systems.

Authors:  Aakarsh Saxena; Felix Perez; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2015-12-09       Impact factor: 15.336

3.  Visible light amination/Smiles cascade: access to phthalazine derivatives.

Authors:  Etienne Brachet; Leyre Marzo; Mohamed Selkti; Burkhard König; Philippe Belmont
Journal:  Chem Sci       Date:  2016-05-06       Impact factor: 9.825

4.  Synthesis of 4-(1H-isochromen-1-yl)isoquinolines through the silver-catalysed homodimerization of ortho-alkynylarylaldehydes and subsequent condensation of the 1,5-dicarbonyl motif with NH3.

Authors:  Minghui Guo; Xin Meng; Yang Zhao; Yuexia Dong; Xuejun Sun; Laijin Tian; Ziping Cao
Journal:  RSC Adv       Date:  2019-01-21       Impact factor: 4.036

5.  Selective oxymetalation of terminal alkynes via 6-endo cyclization: mechanistic investigation and application to the efficient synthesis of 4-substituted isocoumarins.

Authors:  Yuji Kita; Tetsuji Yata; Yoshihiro Nishimoto; Kouji Chiba; Makoto Yasuda
Journal:  Chem Sci       Date:  2018-06-15       Impact factor: 9.825

  5 in total

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