Synlett 2020; 31(09): 903-906
DOI: 10.1055/s-0039-1690850
letter
© Georg Thieme Verlag Stuttgart · New York

Ligand-Free and Solvent-Free Synthesis of 1,3-Disubstituted Naphthalenes through Stille Coupling

Sanae Sbi
a   Laboratory of Analytical and Molecular Chemistry, Department of Chemistry, University Cadi Ayyad, Faculty Polydisciplinaire of Safi, Sidi Bouzid 46000 Safi, Morocco   Email: taoufik.rohand@uca.ac.ma
,
Victor Mkpenie
b   Department of Chemistry, University of Uyo, P. M. B. 1017, Uyo, Nigeria
,
Kiyoshi Tanemura
c   Chemical Laboratory, School of Life Dentistry at Niigata, Nippon Dental University, Hamaura-cho, Niigata 951-8580, Japan
,
a   Laboratory of Analytical and Molecular Chemistry, Department of Chemistry, University Cadi Ayyad, Faculty Polydisciplinaire of Safi, Sidi Bouzid 46000 Safi, Morocco   Email: taoufik.rohand@uca.ac.ma
› Author Affiliations
T.R. is grateful to the University Cadi Ayyad, especially the Faculty Polydisciplinaire of Safi, for the financial support given to the Laboratory of Analytical and Molecular Chemistry. K.T. thanks Nippon Dental University for the financial support to the Chemical Laboratory.
Further Information

Publication History

Received: 14 January 2020

Accepted after revision: 18 February 2020

Publication Date:
20 March 2020 (online)


Abstract

A variety of 1,3-disubstituted naphthalenes have been prepared by palladium-catalyzed annulation of (o-ethynylphenyl)acetyl chloride with design of a new synthetic strategy by Stille coupling using functionalized organostannanes. The method affords excellent yields of the substituted naphthalenes and accommodates a wide variety of functional groups under mild conditions. Mechanistic studies show intramolecular cyclization as a major step following C–C bond coupling.

Supporting Information

 
  • References and Notes

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