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NHC-catalyzed β-specific addition of N-based nucleophiles to allenoates

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Abstract

N-Heterocyclic carbene (NHC) catalyzed regiospecific β-additions of nitrogen-containing nucleophiles including nitrogenous heterocycles and trifluoromethylated acylhydrazone to allenoates were accomplished under mild reaction conditions, harnessing NHC as a Lewis base to furnish branched N-alkyl compounds in moderate to good yields with high E/Z selectivity and broad substrate scope. DFT calculations on the possible reaction mechanisms show that the β-addition pathway is more energetically favourable than the γ-addition pathway, which is in agreement with the experimental observations.

Graphical abstract: NHC-catalyzed β-specific addition of N-based nucleophiles to allenoates

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Article information


Submitted
09 Feb 2020
Accepted
10 May 2020
First published
11 May 2020

Org. Chem. Front., 2020, Advance Article
Article type
Research Article

NHC-catalyzed β-specific addition of N-based nucleophiles to allenoates

W. Wu, S. Xu, Y. Zhang, X. Wang, R. Li, F. Sun, C. Yu, T. Li, D. Wei and C. Yao, Org. Chem. Front., 2020, Advance Article , DOI: 10.1039/D0QO00189A

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