One-Pot, Three-Aryne Cascade Strategy for Naphthalene Formation from 1,3-Diynes and 1,2-Benzdiyne Equivalents

Xiao Xiao, Thomas R Hoye

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

Here we disclose a cascade strategy for naphthyne formation that capitalizes on the traditional benzyne generation (i.e., from an ortho-silyl aryl triflate) and the thermal hexadehydro-Diels-Alder (HDDA) reaction. In this transformation, three distinct aryne species work in tandem, two of which can be formally considered as a 1,2-benzidyne, and each undergoes a different type of trapping event. Many examples were explored by varying the naphthyne capture chemistry as well as the 1,2-benzdiyne equivalent. This strategy enables rapid construction of various naphthalene products and has potential for the synthesis of extended polycyclic arenes.

Original languageEnglish (US)
Pages (from-to)9813-9818
Number of pages6
JournalJournal of the American Chemical Society
Volume141
Issue number25
DOIs
StatePublished - Jun 26 2019

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Diynes
Cycloaddition Reaction
Naphthalene
Hot Temperature
benzyne
naphthalene

PubMed: MeSH publication types

  • Journal Article

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One-Pot, Three-Aryne Cascade Strategy for Naphthalene Formation from 1,3-Diynes and 1,2-Benzdiyne Equivalents. / Xiao, Xiao; Hoye, Thomas R.

In: Journal of the American Chemical Society, Vol. 141, No. 25, 26.06.2019, p. 9813-9818.

Research output: Contribution to journalArticle

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