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, 2-yl)isoindolin-1-one (2c): White solid, yield = 84%, 79.1 mg. Mp: 162-164 o C. 1 H NMR (400 MHz, CDCl3): ? = 7.92 (d, J = 7.2 Hz, 1H), 7.51-7.43 (m, 2H), 7.41-7.36 (m, 3H), 7.31-7.22 (m, 4H)
, 3H) ppm. 13 C{ 1 H} NMR (100 MHz, CDCl3): ? = 169
, ppm. HRMS (ESI) calcd. for
, 2-yl)isoindolin-1-one (2d): White solid, yield = 86%, 82.8 mg. Mp: 121-123 o C. 1 H NMR (400 MHz, CDCl3): ? = 7.91 (d, J = 7.2 Hz, 1H), 7.53-7.42 (m, 5H), 7.37-7.34 (m, 2H), vol.7, pp.33-40
, HRMS (ESI) calcd. for
, -carboxylate (2e): White oil, yield = 55%, 59.2 mg. 1 H NMR (400 MHz, CDCl3): ? = 8
, Hz, 1H), 7.61 (d, J = 8.0 Hz, 1H), 7.54-7.45 (m, 2H), vol.7, p.40
, Hz, 2H), 7.35-7.27 (m, 4H), 4.41 (q, J = 7.2 Hz, 2H), 4.17 (s, 2H), 1.40 (t, J = 7.2 Hz, 3H) ppm. 13 C{ 1 H} NMR (100 MHz, CDCl3): ? = 168, vol.9
, 2-yl)isoindolin-1-one (2j): White solid, yield = 77%, 68.8 mg. Mp: 132-134 o C. 1 H NMR (400 MHz, CDCl3): ? = 7.94 (d, J = 7.6 Hz, 1H), 7.53-7.42 (m, 6H), 7.29-7.26 (m, 3H), vol.7
,
, HRMS (ESI) calcd. for
, 2-yl)isoindolin-1-one (2k): White oil, yield = 79%, 74.5 mg. 1 H NMR (400 MHz, CDCl3): ? = 7.93 (d, J = 6.8 Hz, 1H), 7.51-7.41 (m, 6H), 7.33-7, vol.3
, 2-yl)isoindolin-1-one (2l): Yellow solid, yield = 19%, 16.9 mg. Mp: 108-110 o C. 1 H NMR (400 MHz, CDCl3): ? = 7.92 (d, J = 7.6 Hz, 1H), 7.54-7.43 (m, 6H), 7.38-7.30 (m, 3H)
, JC-F = 21.3 Hz), 52.4 ppm. 19 F{ 1 H} NMR (376 MHz, CDCl3): ? = -114.6 ppm. HRMS (ESI) calcd. for
, 2-yl)isoindolin-1-one (2p): White solid, yield = 55%, 49.7 mg. Mp: 153-155 o C. 1 H NMR (400 MHz, CDCl3): ? = 7.85 (d, J = 7.6 Hz, 1H), 7.53-7.42 (m, 6H), 7.39-7.32 (m, 2H), 7.27-7.21 (m, 1H)
, 141.6, 136.9, 133.9, 132.1, 131.8 (d, JC-F = 1.4 Hz), 131.7, 131.5 (d, JC-F = 3.1 Hz), 129.6 (d, JC-F = 8.0 Hz), 129.3, 128.4, 128.1, 127.9, 126.7 (d, JC-F = 15.4 Hz), vol.124
, 2-yl)isoindolin-1-one (2q): White solid, yield = 74%, 66.7 mg. Mp: 146-148 o C. 1 H NMR (400 MHz, CDCl3): ? = 7.94 (d, J = 6.4 Hz, 1H), 7.52-7.40 (m, 6H), 7.27 (d, J = 7.6 Hz, 1H), 7.22 (s, 1H), 7.20-7.14 (m, 2H), 7.06 (d, J = 7.2 Hz, 1H)
, -yl)isoindolin-1-one (2r): White oil, yield = 32%, 30.7 mg, H NMR (400 MHz, CDCl3): ? = 7.93 (d, J = 7.2 Hz, 1H), 7.53-7.42 (m, 6H), vol.1
, 65 (s, 3H) ppm. 13 C{ 1 H} NMR (100 MHz, CDCl3): ? = 169, Hz, 1H), 7.00-6.94 (m, 2H), 6.82-6.79 (m, 1H), 4.19 (s, 2H), vol.3
, 2-yl)isoindolin-1-one (2s): Yellow solid, yield = 15%, 14.8 mg. Mp: 128-130 o C. 1 H NMR (400 MHz, CDCl3): ? = 7.93 (d, J = 7.2 Hz, 1H), 7.55-7.44 (m, 6H), 7.40 (s, 1H), 7.32 (d, J = 7.2 Hz, 1H), 7.28-7.23 (m, 2H), 7.18 (dd, J = 7.6, 7.6 Hz, 1H), 4.23 (s, 2H) ppm. 13 C{ 1 H} NMR (100 MHz
, Mp: 226-228 o C. 1 H NMR (400 MHz, CDCl3): ? = 8.25 (dd, J = 2.0, 2.0 Hz, 1H), 2-yl)isoindolin-1-one (2t): Yellow solid, yield = 60%, 58.8 mg, vol.8
, White solid, yield = 62%, 58.7 mg. Mp: 169-171 o C. 1 H NMR (400 MHz, CDCl3): ? = 7.94 (d, J = 7.2 Hz, 1H), 7.52-7.41 (m, 6H), vol.7, p.1363
, -(Naphthalen-2-yl)phenyl)isoindolin-1-one (2v): White solid, yield = 83%, 83.1 mg. Mp: 204-206 o C. 1 H NMR (400 MHz, CDCl3): ? = 7.97-7.95 (m, 1H), 7.92 (s, 1H), 7.83-7.77 (m, 2H), 7.73 (d, J = 8.4 Hz, 1H), 7.60-7.57 (m, 1H), 7.56-7.44 (m, 8H), 7.19-7.17 (m, 1H), 4.17 (s, 2H) ppm. 13 C{ 1 H} NMR (100 MHz, CDCl3): ? = 169
, 82 (s, 1H), 7.69 (d, J = 9, -Methoxynaphthalen-2-yl)phenyl)isoindolin-1-one (2w): Brown solid, yield = 70%, 76.7 mg. Mp: 176-178 o C. 1 H NMR (400 MHz, CDCl3): ? = 7.96-7.94 (m, 1H), vol.7
, HRMS (ESI) calcd. for
, Naphthalen-1-yl)phenyl)isoindolin-1-one (2x): Brown oil, yield = 10%, 9, vol.8
, 400 MHz, CDCl3): ? = 7.83-7.75 (m, 4H), 7.62 (d, J = 8.0 Hz, 1H), 7.58-7.35 (m, 9H), 7.09 (d, J = 8.0 Hz, 1H), 4.02 (d, J = 16.8 Hz, 1H), 3.87 (d, J = 16.8 Hz, 1H) ppm. 13 C{ 1 H} NMR (100 MHz, CDCl3): ? = 168.6, 141.5, 137.9
, mol%), KOAc (20 mol%) and K2CO3 (0.15 mmol, 1.5 equiv.) in NMP (0.5 mL) was stirred under Argon for 24 h at 150 °C. After being cooled to ambient temperature, the reaction mixture was diluted with DCM and then filtered through Celite. After evaporation of the solvent in vacuo, the crude product was analyzed by 1 H NMR spectroscopy studies. Crystallographic details: CCDC 1910249-1910254 (2c, 2d, 2g, 2o, 2s, 2q) contains the supplementary crystallographic data for this chapter, General procedure for the attempt of ruthenium-catalyzed arylation reactions using bromobenzene as aryl source
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, -oxoisoindolin-2-yl)phenyl)pyrrolidine-2,5-dione (2a): Brown solid, yield = 92%, 147.4 mg. Mp: 162-164 o C. 1 H NMR (400 MHz, CDCl3): ? = 7.84 (d, J = 7.6 Hz, 1H), 7.58 (dd, J = 7.6, 7.2 Hz, 1H), 7.50-7.46 (m, 2H), 7.40-7.34 (m, 2H), 7.28-7.25 (m, 1H)
, Hz, 1H), 2.97 (dd, J = 18.4, 5.2 Hz, 1H), 2.76 (s, 3H) ppm. 13 C{ 1 H} NMR (100 MHz, CDCl3): ? = 177, vol.9
, Methyl-3-(5-methyl-2-(1-oxoisoindolin-2-yl)phenyl)pyrrolidine-2,5-dione (2b): Brown solid, yield = 88%, 148.0 mg. Mp: < 50 o C. 1 H NMR (400 MHz, CDCl3): ? = 7.83 (d, J = 8.0 Hz, 1H), vol.7
,
, Hz, 1H), 2.77 (s, 3H), 2.34 (s, 3H) ppm. 13 C{ 1 H} NMR, vol.8
, -Methoxy-2-(1-oxoisoindolin-2-yl)phenyl)-1-methylpyrrolidine-2,5-dione (2c): White solid, yield = 91%, 160.0 mg. Mp: 167-169 o C. 1 H NMR (400 MHz, CDCl3): ? = 7.78 (d, J = 7.6 Hz, 1H), 7.53 (dd, J = 7.6, 7.2 Hz, 1H)
, , vol.6
, C{ 1 H} NMR (100 MHz, CDCl3): ? = 177, vol.7
, -Chloro-2-(1-oxoisoindolin-2-yl)phenyl)-1-methylpyrrolidine-2,5-dione (2d): White solid, yield = 96%, 170.0 mg. Mp: 192-194 o C. 1 H NMR (400 MHz, CDCl3): ? = 7.87 (d, J = 7.2 Hz, 1H), vol.7
,
3.01 (dd, J = 18.4, 5.2 Hz, 1H), 2.82 (s, 3H) ppm ,
, HRMS (ESI) calcd. for
, Ethyl 3-(1-methyl-2,5-dioxopyrrolidin-3-yl)-4-(1-oxoisoindolin-2-yl)benzoate (2e): Yellow solid, yield = 70%, 136.9 mg. Mp: < 50 o C. 1 H NMR (400 MHz, CDCl3): ? = 7.97
, Hz, 1H), 7.43 (dd, J = 7.6, 7.2 Hz, 2H), vol.7
,
,
, C{ 1 H} NMR (100 MHz, CDCl3): ? = 177.4, 175.9
, Brown solid, yield = 85%, 155.0 mg. Mp > 260 o C dec. 1 H NMR (400 MHz, CDCl3): ? = 7.88 (d, J = 7.6 Hz, 1H), vol.7, p.95
(m, 2H), 2.85 (s, 3H) ppm ,
, HRMS (ESI) calcd. for
, Methyl-3-(4-methyl-2-(1-oxoisoindolin-2-yl)phenyl)pyrrolidine-2,5-dione (2h): White solid, yield = 66%, 109.9 mg. Mp: 153-155 o C. 1 H NMR (400 MHz, CDCl3): ? = 7.85 (d, J = 8.4 Hz, 1H), 7.58 (dd, J = 7.2, 7.2 Hz, 1H), vol.7
, -Methoxy-2-(1-oxoisoindolin-2-yl)phenyl)-1-methylpyrrolidine-2,5-dione (2i): White solid, yield = 76%, 132.9 mg. Mp: 154-156 o C. 1 H NMR (400 MHz, CDCl3): ? = 7.87 (d, J = 7.6 Hz, 1H)
, , vol.6
, Hz, 1H), 3.78 (s, 3H), 3.15 (dd, J = 18, Hz, 1H), 2.96 (dd, J = 18.8, 4.8 Hz, 1H), 2.79 (s, 3H) ppm. 13 C{ 1 H} NMR (100 MHz, CDCl3): ? = 178, vol.6, p.1162
, Mp: 140-142 o C. This compound exists as a mixture (63:37) of two diastereo-atropoisomers due to the blocked rotation through the N-C(aryl) axis. 1 H NMR (400 MHz, CDCl3): ? = 7.89 (d, J = 7.6 Hz, 1H, major), 7.83 (d, J = 7.6 Hz, 1H, minor), 7.62-7.57 (m, 1H, major), 7.62-7.57 (m, 1H, minor), 7.52-7.45 (m, 2H, major), 7.52-7.45 (m, 2H, minor), 7.40-7.33 (m, 1H, major), 7.40-7.33 (m, 1H, minor), 7.18-7.13 (m, 1H, major), vol.7
, , vol.159
, Hz), 44.7 (d, JC-F = 2.6 Hz), vol.41
, CDCl3): ? = -118.8 (major), -119.4 (minor) ppm. HRMS (ESI) calcd. for
, -Oxoisoindolin-2-yl)phenyl)-1-phenylpyrrolidine-2,5-dione (2l): Brown solid, yield = 78%, 149.0 mg. Mp: 246-248 o C. 1 H NMR (400 MHz, CDCl3): ? = 7.93 (d, J = 7.6 Hz, 1H), 7.61 (dd, J = 7.6, 7.2 Hz, 1H), vol.7
,
, HRMS (ESI) calcd. for
, -oxoisoindolin-2-yl)phenyl)pyrrolidine-2,5-dione (2m): White solid, yield = 76%, 60.9 mg. Mp: < 50 o C. This compound exists as a mixture (53:47) of two diastereo-atropoisomers due to the blocked rotation, vol.1
, .13 (m, 2H) ppm. 13 C{ 1 H} NMR (100 MHz, CDCl3): ? = 176.2, 174.6 (d, JC-F = 17.9 Hz), vol.7, p.247
, 7 (d, JC-F = 19.2 Hz), 54.2, 42.3, 37.3 (d, JC-F = 31.6 Hz) ppm (two carbon peaks overlap with another ones), 3, 123.1, 119.8 (d, JC-F = 5.0 Hz), vol.116, pp.19-20
, CDCl3): ? = -119.2, -119.7 ppm. HRMS (ESI) calcd. for
-oxoisoindolin-2-yl)phenyl)pyrrolidine-2,5-dione (2n): Brown solid, yield = 64%, 88.8 mg. Mp: 136-138 o C ,
, 400 MHz, CDCl3): ? = 7.94 (dd, J = 7.2, 6.4 Hz, vol.1
, -oxoisoindolin-2-yl)phenyl)pyrrolidine-2,5-dione (2o): Brown solid, yield = 70%
, CDCl3): ? = 8.13 (d, J = 8.4 Hz, 2H), 7.89 (d, J = 7.6 Hz, 1H), 7.61 (dd, J = 7.6, 7.2 Hz, 1H), vol.7
, Hz, 1H), 3.36 (d, J = 8.4 Hz, 2H) ppm. 13 C{ 1 H} NMR, vol.100
, -oxoisoindolin-2-yl)phenyl)pyrrolidine-2,5-dione (2p): Brown solid, yield = 88%, 174.0 mg, Mp: < 50 o C. 1 H NMR (400 MHz, CDCl3): ? = 7.90 (d, J = 7.6 Hz, 1H), 7.61 (dd, J = 7.6, 7.2 Hz, 1H), 7.54-7.49 (m, 2H), 7.42-7, vol.3
, HRMS (ESI) calcd. for
, -Oxoisoindolin-2-yl)phenyl)-1-(4-(trifluoromethyl)benzyl)pyrrolidine-2,5-dione (2q): White solid, yield = 88%, 81.3 mg. Mp: 78-80 o C. 1 H NMR (400 MHz, CDCl3): ? = 7.89 (d, J = 7.6 Hz, 1H), 7.62 (dd, J = 7.6, 7.2 Hz, 1H), 7.54-7.50 (m, 4H), 7.43-7.35 (m, 4H), vol.7
-Oxoisoindolin-2-yl)phenyl)-1-(thiophen-2-ylmethyl)pyrrolidine-2,5-dione (2r): White solid, yield = 58%, 70.1 mg, Mp: 216-218 o C. 1 H NMR (400 MHz, CDCl3): ? = 7.89 (d, J = 7.6 Hz, 1H), 7.62 (dd, J = 7.6, 7.2 Hz, 1H), vol.7, p.3 ,
, Hz, 1H), 3.24 (dd, J = 18, Hz, 1H), 2.97 (dd, J = 18.8, 4.8 Hz, 1H) ppm. 13 C{ 1 H} NMR (100 MHz, CDCl3): ? = 177, vol.6
, HRMS (ESI) calcd. for
, -Oxoisoindolin-2-yl)phenyl)pyrrolidine-2,5-dione (2s): Brown solid, yield = 10%, 14.8 mg. Mp: < 50 o C. 1 H NMR (400 MHz, acetone-d6): ? = 10.08 (s, br, 1H), 7.78 (d, J = 7.6 Hz, 1H), vol.17
,
, 2.95 (dd, J = 18.4, 5.6 Hz, 1H) ppm. 13 C{ 1 H} NMR (100 MHz
, Deuteration experiments
, In an oven dried Schlenk tube, to a solution of isoindolinone 1a (0.1 mmol, 1 equiv.) in DCE (0.45 mL) and D2O (0.05 mL) was added the combined reagents under argon
The Schlenk tube was sealed with a Teflon cap and it was heated to 120 °C for 18 h. The reaction mixture was diluted in DCM and filtered using a silica plug eluting with DCM. The solvent was removed in vacuo and ,
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