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, HPLC Data for (S)-Dimethyl 2-(4-phenanthridine-6-carboxamido) succinate (52c)

, Cyclopropenes

, methyl sulfonyl) oxy) propyl) cycloprop-2-enecarboxylate (29): An oven dry 10 mL round-bottom flask was charged with pent-4-yn-1-yl methane sulfonate (1.278 g, 7.83 mmol, 3 equiv

, The solvent was then removed in vacuo, and the residue was purified by flash column chromatography over silica gel (EtOAc-pentane 10/90) to afford compound 29 as a yellow oil (414 mg, 95 %). Rf = 0.6 (EtOAc-Pentane 10/90), mg, 0.013 mmol, 0.005 equiv). A solution of ethyl diazoacetate (200 mg, 1.754 mmol, 1 equiv) in DCM (3.5 mL, 0.5M) was added via a syringe pump over 12 h, vol.834, 0925.

3. Hz, 13 C NMR (75 MHz, CDCl3) ? (ppm) = 176.36, 113.93, 96.11, 68.77, 60.50, 37.44, 26.58, 21.39, 19.83, 14.48. HRMS (ESI): Calcd. For C10H16O5NaS

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M. Ueda, N. Doi, H. Miyagawa, S. Sugita, N. Takeda et al., General procedure for the radical carbocyclization reaction In an oven dry 25 mL two-neck round-bottom flask connected to a reflux condenser, 2-iodo-1-phenylethanone 50a (100 mg, 0.406 mmol, 1 equiv), ethyl 2-propylcycloprop-2-enecarboxylate 51a (250 mg, 1.624 mmol, 4 equiv) and (SnMe3)2 (159.6 mg, 0.487 mmol, 1.2 equiv) were dissolved in benzene (4 mL, 0.1 M) and the reaction mixture was degassed (argon bubbling for 10 min). To this solution was added DTBHN (14 mg, 0.081 mmol, 0.2 equiv) and the reaction mixture was allowed to warm to 65°C for 2 h. Then the solvent was removed in vacuo, and the residue purified by flash column chromatography over silica gel, vol.51, 2015.

, Ethyl 2-iodo-3-(2-oxo-2-phenylethyl)-2-propylcyclopropanecarboxylate 27: Rf = 0.5 (Et2O-pentane 10/90 developed two times). IR (ATR) ?max (cm -1 )

, MHz, CDCl3) ? (ppm) = 7.97 (dd, J = 8.4, 1.3 Hz, 2H), 7.60 -7.56 (m, 1H), 1036.

, 73 -1.65 (m, 1H), 1.48 -1.40 (m, 1H), 1.35 (q, J = 6.8 Hz, 1H), 1.29 (t, J = 7.1 Hz, 3H), 0.94 (t, J = 7.4 Hz, 3H). 13 C-NMR (150 MHz, CDCl3) ? (ppm) = 197

, MHz, CDCl3) ? (ppm) = 8.01 -7.96 (m, 1H), 7.59 -7.54 (m, 2H), vol.7, 1024.

, IR (ATR) ?max (cm -1 ) = 2960, MHz, CDCl3) ? (ppm) = 8.17 (d, J = 7.5 Hz, 1H), 7.61 -7.55 (m, 1H), vol.7, 1035.

, General Procedure C for Carboarylation of Cyclopropene A 25 mL oven dry one-neck round-bottom flask, equipped with a magnetic stirring bar, was charged sequentially with the photocatalyst fac-Ir(ppy)3 (0.02 equiv), the cyclopropene derivative (2 equiv), lithium bromide (2 equiv), potassium carbonate (2 equiv) and 2-bromo-1-arylethanone (1 equiv) under air and

, The reaction mixture was carefully degassed (freeze-pump thaw three times using liquid N2) and refilled with argon, then stirred at room temperature under blue LED irradiation for 12 hours. Blue LED was then switched off and the reaction mixture heated at 60°C for 24h. Finally, the reaction mixture was quenched by addition of water

, Ethyl 2-(4-oxo-1-propyl-1,4-dihydronaphthalen-1-yl)acetate: 42a (60 mg) was obtained through general procedure C in 44% yield as a yellow oil

. =--56, , vol.42

, 1 H-NMR (300 MHz, CDCl3) ? (ppm) = 8.05 (d, J = 8.0 Hz, 1H), mg) was obtained through general procedure C in 40% yield as a yellow oil, vol.815, 1160.

, mg) was obtained through general procedure C in 37% yield as a yellow oil. Rf = 0.19 (EtOAc-Pentane 20/80), 1161.

. Hz,

, m, 1H), 0.97 (t, J = 7.1 Hz, 3H

. Mhz,

, -methoxy-4-oxo-1-propyl-1,4-dihydronaphthalen-1-yl)acetate: 42d (52 mg) was obtained through general procedure C in 34% yield as a yellow oil, Ethyl, vol.2, issue.7

, 1 H-NMR (300 MHz, CDCl3) ? (ppm) = 8.14 (d, J = 8.7 Hz, 1H), 6.97 -6.80 (m, 3H), IR (ATR) ?max (cm -1 ) = 2960, vol.818, 1028.

, mg) was obtained through general procedure C in 31% yield as a yellow oil. IR (ATR) ?max (cm -1 ) = 2960, 1098.

, Hz, 1H), 7.43 (d, J = 2.0 Hz, 1H), vol.7

, m, 2H), 1.12 -1.00 (m, 1H), 0.96 (t, J = 7.1 Hz, 3H

, Ethyl 2-(8-methoxy-4-oxo-1-propyl-1,4-dihydronaphthalen-1-yl)acetate: 42g (60 mg) was obtained through general procedure C in 40 % yield as a yellow oil (r.r. 70:30). Major: Rf = 0, vol.24

, IR (ATR) ?max (cm -1 ) = 2961, 1051.

. Hz, Hz, 3H), 0.69 -0.60 (m, 1H). 13 C-NMR (150 MHz, CDCl3) ? (ppm) = 185.44, 170, (m, 1H), 0.86 (t, J = 7.1 Hz, 3H), 0.74 (t, J = 7, vol.46

, 3-chloropropyl)-4-oxo-1,4-dihydronaphthalen-1-yl)acetate: 42i (63 mg) was obtained through general procedure C in 41 % yield as a yellow oil

, MHz, CDCl3) ? (ppm) = 8.18 (dd, J = 7.8, 1.3 Hz, 1H), 7.65 -7.57 (m, 1H), 7.50 -7.38 (m, 2H), 6.97 -6.91 (m, 1H), 6.57 (d, J = 10.3 Hz, 1H), 1033.

, Ethyl 2-(4-oxo-1-pentyl-1,4-dihydronaphthalen-1-yl)acetate: 42j (61 mg) was obtained through general procedure C in 41 % yield as a yellow oil

, MHz, CDCl3) ? (ppm) = 8.30 -8.03 (m, 1H), 7.63 -7.53 (m, 1H), 7.49 -7.35 (m, 2H), 6.93 (d, J = 10.3 Hz, 1H), 6.54 (d, J = 10.3 Hz, 1H), 1034.

, Calcd. For C19H24NaO3

, butyldimethylsilyl)oxy)propyl)-4-oxo-1,4-dihydronaphthalen-1-yl)acetate: 42k (103 mg) was obtained through general procedure C in 51 % yield as a yellow oil, Rf, vol.0

, MHz, CDCl3) ? (ppm) = 8.18 (dd, J = 7.9, 1.2 Hz, 1H), 7.63 -7.54 (m, 1H), 7.54 -7.35 (m, 2H), vol.836, 1098.

, Ethyl 2-(4-oxo-1-phenethyl-1,4-dihydronaphthalen-1-yl)acetate: 42l (59 mg) was obtained through general procedure C in 35 % yield as a yellow oil

, 1 H-NMR (300 MHz, CDCl3) ? (ppm) = 8.23 (dd, IR (ATR) ?max (cm -1 ) =2929, vol.843, 1030.

, 3.00 (d, J = 14.5 Hz, 1H), 2.86 (d, J = 14.5 Hz, 1H), 2.39 -2.15 (m, 3H), Hz, 1H), 7.00 -6.94 (m, 2H), 6.62 (d, J = 10.3 Hz, 1H), 3.86 (qd, J = 7.1, 1.8 Hz, 2H)

, -acetoxypropyl)-4-oxo-1,4-dihydronaphthalen-1-yl)acetate: 42m (70 mg) was obtained through general procedure C in 42 % yield as a yellow oil, Ethyl, vol.2, issue.1

, IR (ATR) ?max (cm -1 ) = 2960, 1038.

. Mhz, CDCl3) ? (ppm) = 8.17 (dd, J = 7.9, 1.2 Hz, 1H), 7.67 -7.54 (m, 1H), 7.51 -7.38 (m, 2H), vol.6

, Ethyl 2-(1-butyl-4-oxo-1,4-dihydronaphthalen-1-yl)acetate: 42n (66 mg) was obtained through general procedure C in 46 % yield as a yellow oil

, MHz, CDCl3) ? (ppm) = 8.17 (dd, J = 7.9, 1.2 Hz, 1H), vol.7, p.75, 1031.

. Mhz, Calcd. For C18H22NaO3

, Ethyl 2-(1-cyclohexyl-4-oxo-1,4-dihydronaphthalen-1-yl)acetate: 42o (49 mg) was obtained through general procedure C in 31 % yield as a yellow oil

, MHz, CDCl3) ? (ppm) = 8.16 (dd, J = 7.8, 1.2 Hz, 1H), 7.61 -7.53 (m, 1H), vol.840, p.75, 1037.

. Mhz,

, Ethyl 2-(1-cyclopentyl-4-oxo-1,4-dihydronaphthalen-1-yl)acetate: 42p (48 mg) was obtained through general procedure C in 32 % yield as a yellow oil

, IR (ATR) ?max (cm -1 ) = 2953, vol.840, 1028.

. Mhz, CDCl3) ? (ppm) = 8.25 -8.16 (m, 1H), 7.64 -7.49 (m, 2H), 7.41 (dd, J = 6.7, 1.2 Hz, 1H), 7.05 (d, J = 10.4 Hz, 1H), vol.6

, Calcd. For C19H22NaO3

, -bromoethyl)-4-oxo-1,4-dihydronaphthalen-1-yl)acetate: 42q (70 mg) was obtained through general procedure C in 41 % yield as a yellow oil, Ethyl, vol.2, issue.1

, Rf = 0.625 (EtOAc-Pentane 15/85)

, IR (ATR) ?max (cm -1 ) = 2979, vol.842, 1033.

C. Nmr, 75 MHz, CDCl3) ? (ppm)

, Ethyl 2-(4-oxo-1-propyl-1,4-dihydrodibenzo[b,d]furan-1-yl)acetate: 42r (25 mg) was obtained through general procedure C in 16 % yield as a yellow oil

=. Rf, , vol.25

, MHz, CDCl3) ? (ppm) = 7.81 -7.75 (m, 1H), vol.7, 1108.

, mg) was obtained through general procedure C in 24 % yield as a yellow oil. Rf = 0.19 (EtOAc-Pentane 20/80 developed two times). IR (ATR) ?max (cm -1 ) = 2958, p.830, 1030.

H. , 300 MHz, CDCl3) ? (ppm) = 6.81 (d, J = 2.6 Hz, 1H), 6.77 (d, J = 10.1 Hz, 1H), vol.6

. Hz, CDCl3) ? (ppm) = 177.59, 170, vol.18

, 7-dihydrobenzo[b]thiophen-4-yl)acetate: 42t (51 mg) was obtained through general procedure C in 37 % yield as a yellow oil

, 7.12 (d, J = 5.1 Hz, 1H), 6.94 (d, J = 10.1 Hz, 1H), 6.46 (d, J = 10.1 Hz, 1H), 3.91 (qd, J = 7.1, 2.7 Hz, 2H), 2.82 (s, 2H), 1.99 -1.76 (m, 2H), MHz, CDCl3) ? (ppm) = 7.67 (d, J = 5.1 Hz, 1H), vol.830, 1035.

, In a 5 mL oven dry one-neck round-bottom flask, equipped with a magnetic stirring bar, was dissolved in methanol (0.6 mL, 0.2 M), ethyl 2-(1-(3-acetoxypropyl)-4-oxo-1,4-dihydronaphthalen-1-yl)acetate 42m (35 mg, 0.106 mmol, 1 equiv) and potassium carbonate (29 mg, 0.212 mmol, 2 equiv). The reaction mixture was then stirred at room temperature for 12 h. Ethyl acetate (10 mL) was then added and the organic layer washed with water (3 x 5 mL), with brine and dried over sodium sulfate. Then the solvent was removed in vacuo and the residue purified by flash chromatography over silica gel, vol.6

, IR (ATR) ?max (cm -1 ), p.768, 1098.

H. Nmr, 300 MHz, CDCl3) ? (ppm) = 8.11 (dd, J = 8.0, 1.5 Hz, 1H), 7.62 -7.53 (m, 1H), 7.43 -7.33 (m, 2H)

C. Nmr, 75 MHz, CDCl3) ? (ppm) = 195, vol.50

, Following the general procedure C, using photocatalyst fac-Ir(ppy)3 (6.6 mg, 0.010 mmol, 0.02 equiv), ethyl 2-(3-((methyl sulfonyl) oxy)propyl)cycloprop-2-enecarboxylate 7 (189 mg, 1 mmol, 2 equiv), lithium bromide (87 mg, 1 mmol, 2 equiv), potassium carbonate (138 mg, 1 mmol, 2 equiv) and 2-bromo-1-phenylethanone 1b (100 mg, 0.5 mmol, 1 equiv) in anhydrous DMF (2.5 mL, 0.2 M) under argon. After stirring at 20°C under blue LED irradiation for 12 hours, then heating at 60°C for 24h without blue LED, the reaction mixture was quenched with water (10 mL) then extracted with ethyl acetate (50 mL). The residue was purified by flash column chromatography over silica gel

, Rf = 0.1 (EtOAc-Pentane 10/90)

, 45 -7.39 (m, 1H), 6.94 (d, J = 10.3 Hz, 1H), 6.57 (d, J = 10.3 Hz, 1H), 3.87 (qd, 913,745. 1 H NMR (300 MHz, CDCl3) ? 8.20 -8.17 (m, 1H), 7.61 (ddd, J = 8.0, 7.2, 1.5 Hz, 1H), 7.50 -7.46 (m, 1H), vol.7, 1030.

, Then the aqueous layer was extracted with Et2O (3 x 10 mL). The organic layer was then washed with brine and dried over sodium sulfate, filtered, concentrated to afford the desired product as a yellow oil (20 mg, 91 %), which was subjected to the next step without further purification. A solution of Bu3SnH (0.02 mL, 0.1 mmol, 2 equiv), and AIBN (3 mg, 0.02 mmol, 0.4 equiv) in dry benzene (0.5 mL, 0.1M) was added over 5 h by syringe pump to a stirred and heated (85 ? C) solution of the ethyl 2-(1-(3-iodopropyl)-4-oxo-1,4-dihydronaphthalen-1-yl)acetate (20 mg, 0.05 mmol, 1 equiv) in dry benzene (0.5 mL, 0.1M). Heating was continued for 12 hours after the addition. Evaporation of the solvent and flash chromatography of the residue over KF, mL oven dry one-neck round-bottom flask was equipped with a magnetic stirring bar, then charged sequentially with ethyl

, IR (ATR) ?max (cm -1 ) = 2923, pp.769-770, 1031.