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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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. |
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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 |
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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. |
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School of Chemical and Biomedical Engineering |
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School of Chemical and Biomedical Engineering Tatina, Madhu Babu Wang, Xinzhu Santoso, Mardi Moussa, Ziad Judeh, Zaher M. A. |
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Article |
author |
Tatina, Madhu Babu Wang, Xinzhu Santoso, Mardi Moussa, Ziad Judeh, Zaher M. A. |
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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 |
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2021 |
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https://hdl.handle.net/10356/153874 |
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