doi: 10.1002/anie.201900495.
Epub 2019 Mar 18.
Manganese(I)-Catalyzed C-H Activation/Diels-Alder/retro-Diels-Alder Domino Alkyne Annulation featuring Transformable Pyridines
Affiliations
- PMID: 30753749
- DOI: 10.1002/anie.201900495
Item in Clipboard
Manganese(I)-Catalyzed C-H Activation/Diels-Alder/retro-Diels-Alder Domino Alkyne Annulation featuring Transformable Pyridines
Angew Chem Int Ed Engl.
.
Abstract
Complexity-increasing Domino reactions comprising C-H allenylation, a Diels-Alder reaction, and a retro-Diels-Alder reaction were realized by a versatile catalyst derived from earth-abundant, non-toxic manganese. The C-H activation/Diels-Alder/retro-Diels-Alder alkyne annulation sequence provided step-economical access to valuable indolone alkaloid derivatives through a facile organometallic C-H activation manifold with transformable pyridines.
Keywords: C−H activation; domino reactions; indolone alkaloids; manganese; pericyclic reactions.
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
Similar articles
-
Mn-Catalyzed Dehydrocyanative Transannulation of Heteroarenes and Propargyl Carbonates through C-H Activation: Beyond the Permanent Directing Effects of Pyridines/Pyrimidines.Angew Chem Int Ed Engl. 2019 Apr 1;58(15):5090-5094. doi: 10.1002/anie.201900166. Epub 2019 Mar 12. Angew Chem Int Ed Engl. 2019. PMID: 30767347
-
Synthesis and Utility of 2,2-Dimethyl-2 H-pyrans: Dienes for Sequential Diels-Alder/Retro-Diels-Alder Reactions.Org Lett. 2018 Dec 21;20(24):7987-7990. doi: 10.1021/acs.orglett.8b03558. Epub 2018 Dec 11. Org Lett. 2018. PMID: 30525705
-
The oxide anion accelerated retro-diels-alder reaction.Chemistry. 1997 Feb;3(2):187-92. doi: 10.1002/chem.19970030204. Chemistry. 1997. PMID: 24022946
-
Application of the aza-Diels-Alder reaction in the synthesis of natural products.Org Biomol Chem. 2017 Apr 11;15(15):3105-3129. doi: 10.1039/c6ob02761j. Org Biomol Chem. 2017. PMID: 28327756 Review.
-
Exo-Selective Diels-Alder Reactions.Chemistry. 2024 Mar 20;30(17):e202304371. doi: 10.1002/chem.202304371. Epub 2024 Feb 27. Chemistry. 2024. PMID: 38412422 Review.
Cited by
-
Recent Advances on Synthetic Methodology Merging C-H Functionalization and C-C Cleavage.Molecules. 2020 Dec 13;25(24):5900. doi: 10.3390/molecules25245900. Molecules. 2020. PMID: 33322116 Free PMC article. Review.
-
Skeletal editing of pyridines to aryldialdehydes.Nat Commun. 2025 Aug 4;16(1):7133. doi: 10.1038/s41467-025-62627-8. Nat Commun. 2025. PMID: 40759905 Free PMC article.
-
Skeletal editing of pyridines through atom-pair swap from CN to CC.Nat Chem. 2024 May;16(5):741-748. doi: 10.1038/s41557-023-01428-2. Epub 2024 Jan 18. Nat Chem. 2024. PMID: 38238464 Free PMC article.
Grants and funding
LinkOut - more resources
Full Text Sources
