TY - JOUR
T1 - TMSOTf-Promoted Intermolecular Cascade Reaction of Aromatic Diazo Ketones with Olefins
T2 - Selective Synthesis of 3-Arylethylideneoxindoles
AU - Tatina, Madhu Babu
AU - Xinzhu, Wang
AU - Santoso, Mardi
AU - Moussa, Ziad
AU - Judeh, Zaher M.A.
N1 - Funding Information:
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.
Publisher Copyright:
Copyright © 2020 American Chemical Society.
PY - 2020/7/17
Y1 - 2020/7/17
N2 - 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.
AB - 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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U2 - 10.1021/acs.joc.0c01076
DO - 10.1021/acs.joc.0c01076
M3 - Article
AN - SCOPUS:85089270180
SN - 0022-3263
VL - 85
SP - 9129
EP - 9138
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 14
ER -