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Selectivity in the Formal [2 + 2 + 2] Cycloaromatization of Enyne-Allenes Generated by the Alder-ene Reaction from Triynes.

Author information

Affiliations

  • 1. Department of Chemistry, University of Illinois Chicago, 845 W. Taylor St., Chicago, Illinois 60607, United States.
      Authors
    • Vo DV 1
    • Lee D 1
    (2 authors)
  • 2. College of Chemistry and Materials Engineering, Wenzhou University, 325035 Wenzhou, Zhejiang Province, P. R. China.
      Authors
    • Wu T 2
    • Luo Y 2
    • Xia Y 2
    (3 authors)

ORCIDs linked to this article

Organic Letters, 12 Aug 2024, 26(37):7778-7782
https://doi.org/10.1021/acs.orglett.4c01649 PMID: 39133823 

Abstract 

1,3-Diynyl propiolates undergo the Alder-ene reaction to generate enyne-allenes, which participate in the Diels-Alder reaction to provide products of a formal [2 + 2 + 2] cycloaromatization of three alkynes. Without an external alkyne, enyne-allene reacts with one of the alkyne moieties of 1,3-diynyl propiolate, whereas external alkynes can be used to trap enyne-allene to provide various arene products. The substituents on the dienophilic alkynes have a profound impact on their reactivity. In this Diels-Alder reaction, 1,3-diynes display higher reactivity than monoynes; thus, an excess amount (4-5 equiv) of external monoynes needs to be employed to get good product selectivity.

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Read article at publisher's site: https://doi.org/10.1021/acs.orglett.4c01649

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Funding 

Funders who supported this work.

Division of Chemistry (1)

National Natural Science Foundation of China (1)