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Photocatalyst-Free, Visible-Light-Mediated C–H Perfluoroalkylation of Quinazolin-4(3 H)-ones with perfluoroalkyl Iodides.

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Title: Photocatalyst-Free, Visible-Light-Mediated C–H Perfluoroalkylation of Quinazolin-4(3 H)-ones with perfluoroalkyl Iodides.
Authors: Delouche, Thomas1 (AUTHOR), Gadiry-Diallo, Abdoul1 (AUTHOR), Besson, Thierry1 (AUTHOR), Ogoshi, Sensuke2 (AUTHOR), Fruit, Corinne1 (AUTHOR) corinne.fruit@univ-rouen.fr
Source: Synthesis. Nov2023, Vol. 55 Issue 21, p3670-3684. 15p.
Subjects: Fluoroalkyl compounds, Normal-phase chromatography, Iodides, Materials science, Thin layer chromatography
Abstract: SP 1 sp H NMR (300 MHz, acetone- I d i SB 6 sb ): = 11.66 (s, 1 H, H SB N-H sb ), 8.39 (d, I J i = 8.2 Hz, 1 H, H SB 7 sb ), 8.35 (d, I J i = 2.6 Hz, 1 H, H SB 2 sb ), 8.12 (d, I J i = 8.3 Hz, 1 H, H SB 6 sb ). SP 1 sp H NMR (300 MHz, acetone- I d i SB 6 sb ): = 11.49 (s, 1 H, H SB N-H sb ), 8.78 (d, I J i = 2.3 Hz, 1 H, H SB 5 sb ), 8.46 (d, I J i = 2.3 Hz, 1 H, H SB 7 sb ), 8.30 (d, I J i = 2.8 Hz, 1 H, H SB 2 sb ), 8.17-8.07 (m, 2 H, H SB 10or11 sb ), 8.03-7.94 (m, 2 H, H SB 10or11 sb ). SP 13 sp C NMR (75 MHz, acetone- I d i SB 6 sb ): = 157.11 (d, I J i = 15.3 Hz, C SB 4 sb ), 155.38 (dd, I J i = 263.6, 4.4 Hz, Cq), 150.58 (dd, I J i = 253.0, 4.6 Hz, Cq), 148.32 (Cq), 147.54 (C SB 2 sb ), 121.72 (Cq), 120.75 (d, I J i = 3.6 Hz, Cq), 120.03 (Cq), 120.0-104.00 (m, C SB CF sb ). SP 13 sp C NMR (75 MHz, acetone- I d i SB 6 sb ): = 159.44 (C SB 4 sb ), 155.77 (dd, I J i = 266.4, 19.7 Hz, Cq), 150.08 (dd, I J i = 250.8, 15.1 Hz, Cq), 147.14 (C SB 2 sb ), 146.85-146.21 (m, Cq), 122.57-121.48 (m, Cq), 119.05 (dd, I J i = 18.9, 3.4 Hz, C SB 5 sb ), 118.93-114.64 (m, Cq), 119.00-105.00 (m, C SB CF sb ). SP 13 sp C NMR (75 MHz, acetone- I d i SB 6 sb ): = 159.91 (dt, I J i = 252.3, 5.2 Hz, C SB 6 sb ), 157.63 (d, I J i = 3.8 Hz, C SB 4 sb ), 147.42 (Cq), 146.79 (C SB 2 sb ), 133.10 (d, I J i = 7.3 Hz, Cq), 126.29-125.29 (m, C SB 5,7,8 sb ),, 123.00-105.00 (m, C SB CF sb ). [Extracted from the article]
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Abstract:SP 1 sp H NMR (300 MHz, acetone- I d i SB 6 sb ): = 11.66 (s, 1 H, H SB N-H sb ), 8.39 (d, I J i = 8.2 Hz, 1 H, H SB 7 sb ), 8.35 (d, I J i = 2.6 Hz, 1 H, H SB 2 sb ), 8.12 (d, I J i = 8.3 Hz, 1 H, H SB 6 sb ). SP 1 sp H NMR (300 MHz, acetone- I d i SB 6 sb ): = 11.49 (s, 1 H, H SB N-H sb ), 8.78 (d, I J i = 2.3 Hz, 1 H, H SB 5 sb ), 8.46 (d, I J i = 2.3 Hz, 1 H, H SB 7 sb ), 8.30 (d, I J i = 2.8 Hz, 1 H, H SB 2 sb ), 8.17-8.07 (m, 2 H, H SB 10or11 sb ), 8.03-7.94 (m, 2 H, H SB 10or11 sb ). SP 13 sp C NMR (75 MHz, acetone- I d i SB 6 sb ): = 157.11 (d, I J i = 15.3 Hz, C SB 4 sb ), 155.38 (dd, I J i = 263.6, 4.4 Hz, Cq), 150.58 (dd, I J i = 253.0, 4.6 Hz, Cq), 148.32 (Cq), 147.54 (C SB 2 sb ), 121.72 (Cq), 120.75 (d, I J i = 3.6 Hz, Cq), 120.03 (Cq), 120.0-104.00 (m, C SB CF sb ). SP 13 sp C NMR (75 MHz, acetone- I d i SB 6 sb ): = 159.44 (C SB 4 sb ), 155.77 (dd, I J i = 266.4, 19.7 Hz, Cq), 150.08 (dd, I J i = 250.8, 15.1 Hz, Cq), 147.14 (C SB 2 sb ), 146.85-146.21 (m, Cq), 122.57-121.48 (m, Cq), 119.05 (dd, I J i = 18.9, 3.4 Hz, C SB 5 sb ), 118.93-114.64 (m, Cq), 119.00-105.00 (m, C SB CF sb ). SP 13 sp C NMR (75 MHz, acetone- I d i SB 6 sb ): = 159.91 (dt, I J i = 252.3, 5.2 Hz, C SB 6 sb ), 157.63 (d, I J i = 3.8 Hz, C SB 4 sb ), 147.42 (Cq), 146.79 (C SB 2 sb ), 133.10 (d, I J i = 7.3 Hz, Cq), 126.29-125.29 (m, C SB 5,7,8 sb ),, 123.00-105.00 (m, C SB CF sb ). [Extracted from the article]
ISSN:00397881
DOI:10.1055/a-2054-0482