Synthesis of γ-Lactams from Acrylamides by Single-Carbon Atom Doping Annulation

Fujimoto, Hayato; Nakayasu, Bunta; Tobisu, Mamoru

Journal of the American Chemical Society, 2023, 145(36), 19518-19522

Number of Access:423（2025-08-27 19:11 Counts）

Identifier to cite or link to this item: https://hdl.handle.net/11094/92839

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Title
Synthesis of γ-Lactams from Acrylamides by Single-Carbon Atom Doping Annulation
Creator
NRID
1000010963598 1000010963598
ORCID
0000-0002-2046-4596 0000-0002-2046-4596
researchmap permalink
hayato_fujimoto hayato_fujimoto
Scopus Author ID
57201505771 57201505771
CreatorName
Fujimoto, Hayato
CreatorName
Nakayasu, Bunta
NRID
1000060403143 1000060403143
researchmap permalink
read0156480 read0156480
Scopus Author ID
6506514402 6506514402
ORCID
0000-0002-8415-2225 0000-0002-8415-2225
CreatorName
Tobisu, Mamoru
Description
Fujimoto H., Nakayasu B., Tobisu M.. Synthesis of γ-Lactams from Acrylamides by Single-Carbon Atom Doping Annulation. Journal of the American Chemical Society 145, 19518 (2023); https://doi.org/10.1021/jacs.3c07052.
Abstract
A protocol for single-carbon atom doping annulation is reported, which enables the conversion of acrylamides into homologated γ-lactams through the cleavage of two σ-bonds and the formation of four new σ-bonds at the single carbon center. The key strategy is the use of N-heterocyclic carbenes as an atomic carbon equivalent by acting as carbon atom donors through the loss of a 1,2-diimine moiety. Experimental and computational studies reveal that the reaction proceeds through a spirocyclic intermediate, followed by the disassembly of the N-heterocyclic carbene skeleton via proton transfer.
Publisher
American Chemical Society
Source Title
Journal of the American Chemical Society
Volume (Issue)
145(36)
Page
19518-19522
Date of Issued
2023-09-13
Language
English
Handle URL
https://hdl.handle.net/11094/92839
PISSN
00027863
eISSN
15205126
Relation.isVersionOf
DOI (Publisher Version)
https://doi.org/10.1021/jacs.3c07052
Access Rights
open access
CopyRight
This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of the American Chemical Society, © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work seehttps://doi.org/10.1021/jacs.3c07052
oaire:version
Accepted Manuscript
Category
学術雑誌論文 Journal Article