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

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.

SUBMITTER: Xiao X

PROVIDER: S-EPMC6933537 | biostudies-literature | 2019 Jun

REPOSITORIES: biostudies-literature

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

Xiao Xiao X Hoye Thomas R TR

Journal of the American Chemical Society 20190614 25

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 eq ...[more]

PMID: 31181885

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