Please use this identifier to cite or link to this item: https://hdl.handle.net/10356/153874
Title: TMSOTf-promoted intermolecular cascade reaction of aromatic diazo ketones with olefins : selective synthesis of 3-arylethylideneoxindoles
Authors: Tatina, Madhu Babu
Wang, Xinzhu
Santoso, Mardi
Moussa, Ziad
Judeh, Zaher M. A.
Keywords: Engineering::Chemical engineering
Issue Date: 2020
Source: Tatina, M. B., Wang, X., Santoso, M., Moussa, Z. & Judeh, Z. M. A. (2020). TMSOTf-promoted intermolecular cascade reaction of aromatic diazo ketones with olefins : selective synthesis of 3-arylethylideneoxindoles. The Journal of Organic Chemistry, 85(14), 9129-9138. https://dx.doi.org/10.1021/acs.joc.0c01076
Project: RG 13/18
Journal: The Journal of Organic Chemistry 
Abstract: A simple trimethylsilyl trifluoromethanesulfonate (TMSOTf)-promoted intermolecular cascade reaction of aromatic diazo ketones with olefins has been developed. This method directly gave 3-phenylethylideneoxindoles from 3-diazooxindoles and styrenes with exclusive regioselectivity, chemoselectivity, and E-stereoselectivity. The key to the success of the reaction and higher yields is the elegant use of TMSOTf, which gradually released the active triflic acid promoter in situ. The reaction tolerates a wide substrate scope of 3-diazooxindoles and styrenes with electron-donating and electron-withdrawing groups and works well on the gram scale.
URI: https://hdl.handle.net/10356/153874
ISSN: 0022-3263
DOI: 10.1021/acs.joc.0c01076
Rights: © 2020 American Chemical Society. All rights reserved.
Fulltext Permission: none
Fulltext Availability: No Fulltext
Appears in Collections:SCBE Journal Articles

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