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Sakamoto R, Sakurai S, Maruoka K. Alkylsilyl Peroxides as Alkylating Agents in the Copper-Catalyzed Selective Mono-N-Alkylation of Primary Amides and Arylamines. Chemistry. 2017;23(38):9030-9033doi: 10.1002/chem.201702217.
Sakamoto, R., Sakurai, S., & Maruoka, K. (2017). Alkylsilyl Peroxides as Alkylating Agents in the Copper-Catalyzed Selective Mono-N-Alkylation of Primary Amides and Arylamines. Chemistry (Weinheim an der Bergstrasse, Germany), 23(38), 9030-9033. https://doi.org/10.1002/chem.201702217
Sakamoto, Ryu, et al. "Alkylsilyl Peroxides as Alkylating Agents in the Copper-Catalyzed Selective Mono-N-Alkylation of Primary Amides and Arylamines." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 23,38 (2017): 9030-9033. doi: https://doi.org/10.1002/chem.201702217
Sakamoto R, Sakurai S, Maruoka K. Alkylsilyl Peroxides as Alkylating Agents in the Copper-Catalyzed Selective Mono-N-Alkylation of Primary Amides and Arylamines. Chemistry. 2017 Jul 06;23(38):9030-9033. doi: 10.1002/chem.201702217. Epub 2017 Jun 20. PMID: 28523837.
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Chemistry. 2017 Jul 06;23(38):9030-9033. doi: 10.1002/chem.201702217. Epub 2017 Jun 20.

Alkylsilyl Peroxides as Alkylating Agents in the Copper-Catalyzed Selective Mono-N-Alkylation of Primary Amides and Arylamines.

Chemistry (Weinheim an der Bergstrasse, Germany)

Ryu Sakamoto, Shunya Sakurai, Keiji Maruoka

Affiliations

  1. Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan.

PMID: 28523837 DOI: 10.1002/chem.201702217

Abstract

The copper-catalyzed selective mono-N-alkylation of primary amides or arylamines using alkylsilyl peroxides as alkylating agents is reported. The reaction proceeds under mild reaction conditions and exhibits a broad substrate scope with respect to the alkylsilyl peroxides, as well as to the primary amides and arylamines. Mechanistic studies suggest that the present reaction should proceed through a free-radical process that includes alkyl radicals generated from the alkylsilyl peroxides.

© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: N-alkylations; alkylsilyl peroxides; amines; copper; radicals

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