TMSOTf-promoted intermolecular cascade reaction of aromatic diazo ketones with olefins : selective synthesis of 3-arylethylideneoxindoles

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, a...

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Main Authors: Tatina, Madhu Babu, Wang, Xinzhu, Santoso, Mardi, Moussa, Ziad, Judeh, Zaher M. A.
Other Authors: School of Chemical and Biomedical Engineering
Format: Article
Language:English
Published: 2021
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Online Access:https://hdl.handle.net/10356/153874
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Institution: Nanyang Technological University
Language: English
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spelling sg-ntu-dr.10356-1538742021-12-13T02:04:20Z TMSOTf-promoted intermolecular cascade reaction of aromatic diazo ketones with olefins : selective synthesis of 3-arylethylideneoxindoles Tatina, Madhu Babu Wang, Xinzhu Santoso, Mardi Moussa, Ziad Judeh, Zaher M. A. School of Chemical and Biomedical Engineering Engineering::Chemical engineering Hydrocarbons Aromatic Compounds 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. Nanyang Technological University We thank the Nanyang Technological University, Singapore (grant #RG 13/18), Ministry of Research, Technology and Higher Education, Republic of Indonesia (World Class Professor Program) and the United Arab Emirates University (grant #852) for financial support. 2021-12-13T02:04:20Z 2021-12-13T02:04:20Z 2020 Journal Article 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 0022-3263 https://hdl.handle.net/10356/153874 10.1021/acs.joc.0c01076 32567855 2-s2.0-85089270180 14 85 9129 9138 en RG 13/18 The Journal of Organic Chemistry © 2020 American Chemical Society. All rights reserved.
institution Nanyang Technological University
building NTU Library
continent Asia
country Singapore
Singapore
content_provider NTU Library
collection DR-NTU
language English
topic Engineering::Chemical engineering
Hydrocarbons
Aromatic Compounds
spellingShingle Engineering::Chemical engineering
Hydrocarbons
Aromatic Compounds
Tatina, Madhu Babu
Wang, Xinzhu
Santoso, Mardi
Moussa, Ziad
Judeh, Zaher M. A.
TMSOTf-promoted intermolecular cascade reaction of aromatic diazo ketones with olefins : selective synthesis of 3-arylethylideneoxindoles
description 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.
author2 School of Chemical and Biomedical Engineering
author_facet School of Chemical and Biomedical Engineering
Tatina, Madhu Babu
Wang, Xinzhu
Santoso, Mardi
Moussa, Ziad
Judeh, Zaher M. A.
format Article
author Tatina, Madhu Babu
Wang, Xinzhu
Santoso, Mardi
Moussa, Ziad
Judeh, Zaher M. A.
author_sort Tatina, Madhu Babu
title TMSOTf-promoted intermolecular cascade reaction of aromatic diazo ketones with olefins : selective synthesis of 3-arylethylideneoxindoles
title_short TMSOTf-promoted intermolecular cascade reaction of aromatic diazo ketones with olefins : selective synthesis of 3-arylethylideneoxindoles
title_full TMSOTf-promoted intermolecular cascade reaction of aromatic diazo ketones with olefins : selective synthesis of 3-arylethylideneoxindoles
title_fullStr TMSOTf-promoted intermolecular cascade reaction of aromatic diazo ketones with olefins : selective synthesis of 3-arylethylideneoxindoles
title_full_unstemmed TMSOTf-promoted intermolecular cascade reaction of aromatic diazo ketones with olefins : selective synthesis of 3-arylethylideneoxindoles
title_sort tmsotf-promoted intermolecular cascade reaction of aromatic diazo ketones with olefins : selective synthesis of 3-arylethylideneoxindoles
publishDate 2021
url https://hdl.handle.net/10356/153874
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