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Issue 8, 2017

Rapid access to substituted 2-naphthyne intermediates via the benzannulation of halogenated silylalkynes

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Abstract

Aryne intermediates are versatile and important reactive intermediates for natural product and polymer synthesis. 2-Naphthynes are relatively unexplored because few methods provide precursors to these intermediates, especially for those bearing additional substituents. Here we report a general synthetic strategy to access 2-naphthyne precursors through an Asao-Yamamoto benzannulation of ortho-(phenylethynyl)benzaldehydes with halo-silylalkynes. This transformation provides 2-halo-3-silylnaphthalenes with complete regioselectivity. These naphthalene products undergo desilylation/dehalogenation in the presence of F to generate the corresponding 2-naphthyne intermediate, as evidenced by furan trapping experiments. When these 2-naphthynes are generated in the presence of a copper catalyst, ortho-naphthalene oligomers, trinaphthalene, or binaphthalene products are formed selectively by varying the catalyst loading and reaction temperature. The efficiency, mild conditions, and versatility of the naphthalene products and naphthyne intermediates will provide efficient access to many new functional aromatic systems.

Graphical abstract: Rapid access to substituted 2-naphthyne intermediates via the benzannulation of halogenated silylalkynes

Supplementary files

Article information


Submitted
11 Apr 2017
Accepted
04 Jun 2017
First published
09 Jun 2017

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2017,8, 5675-5681
Article type
Edge Article

Rapid access to substituted 2-naphthyne intermediates via the benzannulation of halogenated silylalkynes

S. J. Hein, D. Lehnherr and W. R. Dichtel, Chem. Sci., 2017, 8, 5675 DOI: 10.1039/C7SC01625E

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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