TY - JOUR
T1 - HFIP-promoted Michael reactions
T2 - direct para-selective C-H activation of anilines with maleimides
AU - Li, Bang
AU - Mao, Qi
AU - Zhou, Jia
AU - Liu, Feng
AU - Ye, Na
N1 - Funding Information:
This work was supported by the National Natural Science Foundation of China (81703330), the Natural Science Foundation of Jiangsu Province (BK20170347), and the Jiangsu Key Laboratory of Neuropsychiatric Diseases (BM2013003). We want to thank Prof. Zhenqing Zhang and Yang Ou in the Department of Pharmaceutical Analysis at Soochow University for HRMS spectroscopy assistance.
Publisher Copyright:
© The Royal Society of Chemistry.
PY - 2019
Y1 - 2019
N2 - The Michael reaction is widely used for the C-C coupling of electron-poor olefins and C(sp 3 )-H pronucleophiles. Herein, an effective Michael reaction approach between electron-rich aromatic and heteroaromatic substrates as C(sp 2 )-H nucleophiles with maleimides as electrophiles in 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) was first presented without the need for any additional metal catalysts or reagents. This reaction provides a concise and environmentally friendly strategy for the facile construction of 3-aryl succinimides from N,N-disubstituted anilines and maleimides with high para selectivity.
AB - The Michael reaction is widely used for the C-C coupling of electron-poor olefins and C(sp 3 )-H pronucleophiles. Herein, an effective Michael reaction approach between electron-rich aromatic and heteroaromatic substrates as C(sp 2 )-H nucleophiles with maleimides as electrophiles in 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) was first presented without the need for any additional metal catalysts or reagents. This reaction provides a concise and environmentally friendly strategy for the facile construction of 3-aryl succinimides from N,N-disubstituted anilines and maleimides with high para selectivity.
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U2 - 10.1039/C8OB03073A
DO - 10.1039/C8OB03073A
M3 - Article
C2 - 30720821
AN - SCOPUS:85061852371
SN - 1477-0520
VL - 17
SP - 2242
EP - 2246
JO - Organic and Biomolecular Chemistry
JF - Organic and Biomolecular Chemistry
IS - 8
ER -