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Title: Cleavage and reassembly C≡C bonds of ynones to access highly functionalized ketones
Authors: Rong, Jiaxin
Li, Haowen
Fu, Rui
Sun, Wangbin
Loh, Teck-Peng
Jiang, Yaojia
Keywords: Science::Biological sciences::Biochemistry
Issue Date: 2020
Source: Rong, J., Li, H., Fu, R., Sun, W., Loh, T. & Jiang, Y. (2020). Cleavage and reassembly C≡C bonds of ynones to access highly functionalized ketones. ACS Applied Materials and Interfaces, 10(6), 3664-3669.
Journal: ACS Applied Materials and Interfaces
Abstract: An economical strategy has been designed to formally cleave CC bonds of ynones through copper-catalyzed carbene chemistry. It proceeds under mild reaction conditions in a step-economy process by simultaneously cleaving the CC bonds and constructing C-C bonds. Depending on the substitution of the ynones, the reactions can proceed efficiently to generate synthetically useful 1,4-ketoaldehydes and cyclopentenone compounds. A plausible pathway is proposed that involves an active cyclopropane intermediate that consequently undergoes a cascade ring-opening reaction. The method works for a spectrum of ynones and N-tosylhydrazones that give good to excellent yields using a cheap copper catalytic system.
ISSN: 1944-8244
DOI: 10.1021/acscatal.0c00381
Schools: School of Physical and Mathematical Sciences 
Rights: © 2020 American Chemical Society. All rights reserved.
Fulltext Permission: none
Fulltext Availability: No Fulltext
Appears in Collections:SPMS Journal Articles

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