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In Situ Allene Formation via Alkyne Tautomerization to Promote [4 + 2]-Cycloadditions with a Pendant Alkyne or Nitrile.
Org Lett. 2022 04 01; 24(12):2327-2331.OL

Abstract

We have explored the net-[4 + 2]-cycloadditions of a variety of aryl (or alkenyl) alkynes. Tautomerization via base-catalyzed alkyne-to-allene isomerization produces a transient allene, which undergoes stepwise cyclization with not only a pendant alkyne but also a nitrile. The operative mechanisms for these reactions were studied by density functional theory and compared with the slower thermal cyclization of the precursor alkyne.

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Authors+Show Affiliations

Kraemer N
Department of Chemistry, University of Minnesota, 207 Pleasant Street SE, Minneapolis, Minnesota 55455, United States.
Naredla RR
Department of Chemistry, University of Minnesota, 207 Pleasant Street SE, Minneapolis, Minnesota 55455, United States.
Hoye TR
Department of Chemistry, University of Minnesota, 207 Pleasant Street SE, Minneapolis, Minnesota 55455, United States.

MeSH

AlkadienesAlkynesCatalysisCycloaddition ReactionNitriles

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural
Research Support, U.S. Gov't, Non-P.H.S.

Language

eng

PubMed ID

35311283

Citation

Kraemer, Niklas, et al. "In Situ Allene Formation Via Alkyne Tautomerization to Promote [4 + 2]-Cycloadditions With a Pendant Alkyne or Nitrile." Organic Letters, vol. 24, no. 12, 2022, pp. 2327-2331.
Kraemer N, Naredla RR, Hoye TR. In Situ Allene Formation via Alkyne Tautomerization to Promote [4 + 2]-Cycloadditions with a Pendant Alkyne or Nitrile. Org Lett. 2022;24(12):2327-2331.
Kraemer, N., Naredla, R. R., & Hoye, T. R. (2022). In Situ Allene Formation via Alkyne Tautomerization to Promote [4 + 2]-Cycloadditions with a Pendant Alkyne or Nitrile. Organic Letters, 24(12), 2327-2331. https://doi.org/10.1021/acs.orglett.2c00491
Kraemer N, Naredla RR, Hoye TR. In Situ Allene Formation Via Alkyne Tautomerization to Promote [4 + 2]-Cycloadditions With a Pendant Alkyne or Nitrile. Org Lett. 2022 04 1;24(12):2327-2331. PubMed PMID: 35311283.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - In Situ Allene Formation via Alkyne Tautomerization to Promote [4 + 2]-Cycloadditions with a Pendant Alkyne or Nitrile. AU - Kraemer,Niklas, AU - Naredla,Rajasekhar Reddy, AU - Hoye,Thomas R, Y1 - 2022/03/21/ PY - 2022/3/22/pubmed PY - 2022/4/5/medline PY - 2022/3/21/entrez SP - 2327 EP - 2331 JF - Organic letters JO - Org Lett VL - 24 IS - 12 N2 - We have explored the net-[4 + 2]-cycloadditions of a variety of aryl (or alkenyl) alkynes. Tautomerization via base-catalyzed alkyne-to-allene isomerization produces a transient allene, which undergoes stepwise cyclization with not only a pendant alkyne but also a nitrile. The operative mechanisms for these reactions were studied by density functional theory and compared with the slower thermal cyclization of the precursor alkyne. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/35311283/In_Situ_Allene_Formation_via_Alkyne_Tautomerization_to_Promote_[4_+_2]_Cycloadditions_with_a_Pendant_Alkyne_or_Nitrile_ DB - PRIME DP - Unbound Medicine ER -