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

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 c

SUBMITTER: Hein SJ 

PROVIDER: S-EPMC5621055 | biostudies-literature | 2017 Aug

REPOSITORIES: biostudies-literature