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Ruthenium-catalyzed cascade C-H activation/annulation of N-alkoxybenzamides : reaction development and mechanistic insight

Liangliang Song, Xiaoyong Zhang, Xiao Tang, Luc Van Meervelt, Johan Van der Eycken (UGent) , Jeremy N. Harvey and Erik V. Van der Eycken
(2020) CHEMICAL SCIENCE. 11(42). p.11562-11569
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Abstract
A highly selective ruthenium-catalyzed C-H activation/annulation of alkyne-tethered N-alkoxybenzamides has been developed. In this reaction, diverse products from inverse annulation can be obtained in moderate to good yields with high functional group compatibility. Insightful experimental and theoretical studies indicate that the reaction to the inverse annulation follows the Ru(ii)-Ru(iv)-Ru(ii) pathway involving N-O bond cleavage prior to alkyne insertion. This is highly different compared to the conventional mechanism of transition metal-catalyzed C-H activation/annulation with alkynes, involving alkyne insertion prior to N-O bond cleavage. Via this pathway, the in situ generated acetic acid from the N-H/C-H activation step facilitates the N-O bond cleavage to give the Ru-nitrene species. Besides the conventional mechanism forming the products via standard annulation, an alternative and novel Ru(ii)-Ru(iv)-Ru(ii) mechanism featuring N-O cleavage preceding alkyne insertion has been proposed, affording a new understanding of transition metal-catalyzed C-H activation/annulation.
Keywords
PROPARGYL ALCOHOLS, 4+1 ANNULATION, INTRAMOLECULAR ANNULATION, OXIDATIVE, ANNULATION, REACTION PATHWAY, BOND ACTIVATION, O BOND, BENZAMIDES, ALKYNES, OXIDANT

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MLA
Song, Liangliang, et al. “Ruthenium-Catalyzed Cascade C-H Activation/Annulation of N-Alkoxybenzamides : Reaction Development and Mechanistic Insight.” CHEMICAL SCIENCE, vol. 11, no. 42, 2020, pp. 11562–69, doi:10.1039/d0sc04434b.
APA
Song, L., Zhang, X., Tang, X., Van Meervelt, L., Van der Eycken, J., Harvey, J. N., & Van der Eycken, E. V. (2020). Ruthenium-catalyzed cascade C-H activation/annulation of N-alkoxybenzamides : reaction development and mechanistic insight. CHEMICAL SCIENCE, 11(42), 11562–11569. https://doi.org/10.1039/d0sc04434b
Chicago author-date
Song, Liangliang, Xiaoyong Zhang, Xiao Tang, Luc Van Meervelt, Johan Van der Eycken, Jeremy N. Harvey, and Erik V. Van der Eycken. 2020. “Ruthenium-Catalyzed Cascade C-H Activation/Annulation of N-Alkoxybenzamides : Reaction Development and Mechanistic Insight.” CHEMICAL SCIENCE 11 (42): 11562–69. https://doi.org/10.1039/d0sc04434b.
Chicago author-date (all authors)
Song, Liangliang, Xiaoyong Zhang, Xiao Tang, Luc Van Meervelt, Johan Van der Eycken, Jeremy N. Harvey, and Erik V. Van der Eycken. 2020. “Ruthenium-Catalyzed Cascade C-H Activation/Annulation of N-Alkoxybenzamides : Reaction Development and Mechanistic Insight.” CHEMICAL SCIENCE 11 (42): 11562–11569. doi:10.1039/d0sc04434b.
Vancouver
1.
Song L, Zhang X, Tang X, Van Meervelt L, Van der Eycken J, Harvey JN, et al. Ruthenium-catalyzed cascade C-H activation/annulation of N-alkoxybenzamides : reaction development and mechanistic insight. CHEMICAL SCIENCE. 2020;11(42):11562–9.
IEEE
[1]
L. Song et al., “Ruthenium-catalyzed cascade C-H activation/annulation of N-alkoxybenzamides : reaction development and mechanistic insight,” CHEMICAL SCIENCE, vol. 11, no. 42, pp. 11562–11569, 2020.
@article{8686590,
  abstract     = {{A highly selective ruthenium-catalyzed C-H activation/annulation of alkyne-tethered N-alkoxybenzamides has been developed. In this reaction, diverse products from inverse annulation can be obtained in moderate to good yields with high functional group compatibility. Insightful experimental and theoretical studies indicate that the reaction to the inverse annulation follows the Ru(ii)-Ru(iv)-Ru(ii) pathway involving N-O bond cleavage prior to alkyne insertion. This is highly different compared to the conventional mechanism of transition metal-catalyzed C-H activation/annulation with alkynes, involving alkyne insertion prior to N-O bond cleavage. Via this pathway, the in situ generated acetic acid from the N-H/C-H activation step facilitates the N-O bond cleavage to give the Ru-nitrene species. Besides the conventional mechanism forming the products via standard annulation, an alternative and novel Ru(ii)-Ru(iv)-Ru(ii) mechanism featuring N-O cleavage preceding alkyne insertion has been proposed, affording a new understanding of transition metal-catalyzed C-H activation/annulation.}},
  author       = {{Song, Liangliang and Zhang, Xiaoyong and Tang, Xiao and Van Meervelt, Luc and Van der Eycken, Johan and Harvey, Jeremy N. and Van der Eycken, Erik V.}},
  issn         = {{2041-6520}},
  journal      = {{CHEMICAL SCIENCE}},
  keywords     = {{PROPARGYL ALCOHOLS,4+1 ANNULATION,INTRAMOLECULAR ANNULATION,OXIDATIVE,ANNULATION,REACTION PATHWAY,BOND ACTIVATION,O BOND,BENZAMIDES,ALKYNES,OXIDANT}},
  language     = {{eng}},
  number       = {{42}},
  pages        = {{11562--11569}},
  title        = {{Ruthenium-catalyzed cascade C-H activation/annulation of N-alkoxybenzamides : reaction development and mechanistic insight}},
  url          = {{http://doi.org/10.1039/d0sc04434b}},
  volume       = {{11}},
  year         = {{2020}},
}
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