Sustainable Radical Cascades to Synthesize Difluoroalkylated Pyrrolo[1,2-a]indoles
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1 Sustainable Radical Cascades to Synthesize Difluoroalkylated Pyrrolo[1,2-a]indoles Honggui Huang a, Menglin Yu a, Xiaolong Su a, Peng Guo a, Jia Zhao a, Jiabing Zhou a and Yi Li a, b * a Department of Chemistry, Fuzhou University, Fuzhou , China b State Key Laboratory of Photocatalysis on Energy and Environment, Fuzhou University, Fuzhou, , China *Corresponding author. address: liyi-chem@fzu.edu.cn S1
2 Table of contents 1. Optimzation details s3 1.1 Optimzation of catalyst s3 1.2 Optimzation of solvent s3 1.3 Optimzation of base s4 1.4 Contral experiments s4 2. Mechanistic studies s6 2.1 Determination of quantum yield s6 2.2 Radical trapping experiments s8 2.3 Emission quenching experiments s8 3. Spectra data (1a-1ac, 2b-2h, 3a-3ak, 4, 5, 6, 7)......S10 S2
3 1 Optimization details 1.1 Optimization of catalyst entry a photocatalyst 3a (%) b 1 fac-ir(ppy) 3 81(71) 2 Ir(dF(CF 3 )ppy) 2 (bpy)(pf 6 ) 25 3 Ir(ppy) 2 (dtppy) n.r. 4 Ru(bpy) 3 Cl 2 n.r. 5 Ru(Phen) 3 (PF 6 ) n.r. 6 9-fluorenone n.r. 7 Methyl blue n.r. 8 Eosin Y n.r. 9 Eosin B n.r. 10 Fluorescein n.r. a Reaction conditions:1 (0.2 mmol), 2(0.5 mmol), photocatalyst (0.002 mmol), Na 2 HPO 4 (0.24 mmol) in THF (2 ml) irradiated by 3 W blue LEDs at room temperature for 12 h. b Determined by crude 19 F NMR with,, -trifluoromethyl benzene as the internal standard. Isolated yields are given in parentheses. 1.2 Optimization of solvent entry a solvent x (M) 3a (%) b 1 DMF DMSO S3
4 3 THF (71) 4 CH 3 CN 0.1 n.r. 5 1,4-dioxane DCM (85) 7 CHCl (84) 8 toluene DCM DCM c DCM d DCM a Reaction conditions:1 (0.2 mmol), 2 (0.5 mmol), fac-ir(ppy) 3 (0.002mmol), Na 2 HPO 4 (0.24 mmol) in solvent (2 ml) irradiated by 3 W blue LEDs at room temperature for 12 h. b Determined by crude 19 F NMR with,, -trifluoromethyl benzene as the internal standard. Isolated yields are given in parentheses. c The amount of fac-ir(ppy) 3 is 0.001mmol. d The amount of fac-ir(ppy) 3 is 0.004mmol. 1.3 Optimization of base entry a base 3a (%) b 1 Na 2 HPO 4 99 (85) 2 K 2 HPO NaHCO 3 n.r. 4 Na 2 CO 3 n.r. 5 K 2 CO 3 n.r. 6 Et 3 N n.r. 7 DBU n.r. a Reaction conditions:1 (0.2 mmol), 2(0.5 mmol), fac-ir(ppy) 3 (0.002 mmol), base (0.24 mmol) in DCM (2 ml) irradiated by 3 W blue LEDs at room temperature for 12 h. b Determined by crude 19 F NMR S4
5 with,, -trifluorometnyl benzene as the internal standard. Isolated yields are given in parentheses. 1.4 Control experiments entry a base photocatalyst 3a (%) b 1 Na 2 HPO 4 fac-ir(ppy) 3 99 (85) 2 c Na 2 HPO 4 fac-ir(ppy) 3 n.r. 3 Na 2 HPO 4 - n.r. 4 - fac-ir(ppy) 3 n.r. a Reaction conditions:1 (0.2 mmol), 2 (0.5 mmol), fac-ir(ppy) 3 (0.002 mmol), Na 2 HPO 4 (0.24 mmol) in DCM (2 ml) irradiated by 3 W blue LEDs at room temperature for 12 h. b Determined by crude 19 F NMR with,, -trifluoromethyl benzene as the internal standard. Isolated yields are given in parentheses. c In dark. S5
6 2. Mechanistic study 2.1 Determination of quantum yield Determination of the light intensity at 365 nm: The photon flux of the spectrophotometer was determined by standard ferrioxalate actinometry g of Potassium ferrioxalate hydrate was dissolved in 30 ml of 0.05 M H 2 SO 4 to prepare a 0.15 M solution of ferrioxalate. A buffered solution of phenanthroline was prepared by dissolving 50 mg of phenanthroline and g of sodium acetate in 50 ml of 0.5 M H 2 SO 4. Both solutions were stored in the dark. To determine the photon flux of the spectrophotometer, 2.0 ml of the ferrioxalate solution was placed in a cuvette and irradiated for 90.0 seconds at λ = 365 nm with an emission slit width at 10.0 nm. After irradiation, 0.35 ml of the phenanthroline solution was added to the cuvette. The solution was then allowed to rest for 1 h to allow the ferrous ions to completely coordinate to the phenanthroline. The absorbance of the solution was measured at 510 nm. A non-irradiated sample was also prepared and the absorbance at 510 nm measured. Conversion was calculated using eq. (1): ol e = (1) Where V is the total volume ( L) of the solution after addition of phenanthroline, ΔA is the difference in absorbance at 510 nm between the irradiated and non-irradiated solutions, l is the path length (1.000 c ), and ε is the molar absorptivity at 510 nm (11100 L mol 1 cm 1 ). The photon flux can be calculated using eq (2): photon fl = ol e (2) Where Φ is the q ant yield for the ferrio alate actino eter (0.15 for a 0.15 M solution at λ =365 nm), t is the time (90.0 s), and f is the fraction of light absorbed at λ =365 nm ( vide infra). The photon flux was calculated to be einstein s 1. Sample calculation: ol e = = ol photon fl = 10 =. 10 einstein s 1 Determination of fraction (light absorbed at 365 nm) for the ferrioxalatesolution The absorbance of the above ferrioxalate solution at 365 nm was measured to be The fraction of light absorbed (f) by this solution was calculated using eq. (3), where A is the measured absorbance at 365 nm. = (3) S6
7 Abs Walvelength (nm) Figure S1.Absorbance of the ferrioxalate actinometer solution. A cuvette was charged with 1a (0.2 mmol, 39.6 mg), 2a (0.5 mmol, 102 mg), fac-ir(ppy) 3 (0.002 mmol, 1.3 mg), Na 2 HPO 4 (0.24 mmol, 34.1 mg) in 2 ml DCM (0.1 M). The cuvette was then capped with a PTFE stopper. The sample was stirred and irradiated (λ = 365 nm, slit width=10.0 nm) for 9 h. After irradiation, the solution was passed through a silica plug. The yield of product formed was determined by flash column chromatography. The quantum yield was determined using eq. (4). Essentially all incident light (f > 0.999, vide infra) is absorbed by the fac-ir(ppy) 3 at the reaction conditions described above: (4) 1a (0.2 mmol, 39.6 mg), 2a (0.5 mmol, 102 mg), fac-ir(ppy) 3 (0.002 mmol, 1.3 mg), Na 2 HPO 4 (0.24 mmol, 34.1 mg) in DCM (2 ml) after 9 h yielded of 3a (three reactions were reacted parallel and 3a obtained in 21 mg). Φ (11%) = Sample quantum yield calculation: 10 5 Φ= 10 1 Absorbance of catalyst = The absorbance of fac-ir(ppy) 3 in DCM was measured at the reaction concentration of M. The absorbance at 365 nm for a M solution is > 3 indicating the fraction of light absorbed is > S7
8 Abs Walvelength (nm) Figure S2. Absorbance of a M solution of fac-ir(ppy) 3 in DCM. 2.2 Radical trapping experiments To a 10 ml sealed tube equipped with a rubber septum and magnetic stir bar, 1a (0.2 mmol, 39.8 mg), fac-ir(ppy) 3 (0.002 mmol, 1.3 mg), Na 2 HPO 4 (0.24 mmol, 32.4 mg) were added. The flask was evacuated and backfilled with nitrogen for 3 times. 2a (0.5 mmol, 101.5mg), TEMPO (0.5 mmol, 78.1 mg) and DCM (2.0 ml) were added under nitrogen. The mixture was then stirred and irradiated by 3W blue LEDs for 15 hours at room temperature.after the reaction was complete (detected by TLC), Thecrude reaction mixture analysis by 19 F NMR showed that TEMPO-CF 2 COOEt (6) was formedand the isolated yield is 40%, meanwhile 2a was not detected. When we added ethene-1,1-diyldibenzene (0.5 mmol, 90.1 mg), 7 was formed and the isolated yield is 41%. 2.3 Emission quenching experiments fac-ir(ppy) 3 + BrCF 2 COOEt under air S8
9 Intensity Intensity I 0 /I-1 Intensity ul 100 ul 150 ul 200 ul 400 ul 600 ul 800 ul y = 2191x R 2 = Wavelength (nm) Concentration of BrCF 2 COOEt Condition: To the solution of fac-ir(ppy) 3 (10 μm) in 2 ml DCM was added BrCF 2 COOEt in different concentrations including 0, 100, 150, 200, 400, 600 and 800 μm at roo te perat re nder air. (Excitation wavelength: 480 nm). fac-ir(ppy) 3 +1a under air ul 50 ul 80 ul 140 ul 240 ul 300 ul Wavelength (nm) Condition: To the solution of fac-ir(ppy) 3 (10 μm) in 2 ml DCM was added 1a in different concentrations including 0, 50, 80, 140, 240 and 300 μm at roo te perat re nder air. (Excitation wavelength: 480 nm). fac-ir(ppy) 3 +Na 2 HPO 4 under air ul 10 ul 20 ul 30 ul 40 ul 50 ul 100 ul 200 ul Wavelength Condition: To the solution of fac-ir(ppy) 3 (10 μm) in 2 ml DCM was added Na 2 HPO 4 in different concentrations including 0, 10, 20, 30, 40, 50, 100 and 200 μm at roo te perat re nder air. (Excitation wavelength: 480 nm). S9
10 3 Spectra data 1 H NMR for 1a (400 MHz, CDCl 3 ) 13 C NMR for 1a (101 MHz, CDCl 3 ) S10
11 1 H NMR for 1b (400 MHz, CDCl 3 ) 13 C NMR for 1b (101 MHz, CDCl 3 ) S11
12 1 H NMR for 1c (400 MHz, CDCl 3 ) 13 C NMR for 1c (101 MHz, CDCl 3 ) S12
13 1 H NMR for 1d (400 MHz, CDCl 3 ) 13 C NMR for 1d (101 MHz, CDCl 3 ) S13
14 19 F NMR for 1d (376 MHz, CDCl 3 ) 1 H NMR for 1e (400 MHz, CDCl 3 ) S14
15 13 C NMR for 1e (101 MHz, CDCl 3 ) 1 H NMR for 1f (400 MHz, CDCl 3 ) S15
16 13 C NMR for 1f (101 MHz, CDCl 3 ) 1 H NMR for 1g (400 MHz, CDCl 3 ) S16
17 13 C NMR for 1g (101 MHz, CDCl 3 ) 1 H NMR for 1h (400 MHz, CDCl 3 ) S17
18 13 C NMR for 1h (101 MHz, CDCl 3 ) 1 H NMR for 1i (400 MHz, CDCl 3 ) S18
19 13 C NMR for 1i (101 MHz, CDCl 3 ) 1 H NMR for 1j (400 MHz, CDCl 3 ) S19
20 13 C NMR for 1j (101 MHz, CDCl 3 ) 1 H NMR for 1k (400 MHz, CDCl 3 ) S20
21 13 C NMR for 1k (101 MHz, CDCl 3 ) 19 F NMR for 1k (376 MHz, CDCl 3 ) S21
22 1 H NMR for 1l (400 MHz, CDCl 3 ) 13 C NMR for 1l (101 MHz, CDCl 3 ) S22
23 1 H NMR for 1m (400 MHz, CDCl 3 ) 13 C NMR for 1m (101 MHz, CDCl 3 ) S23
24 1 H NMR for 1n (400 MHz, CDCl 3 ) 13 C NMR for 1n (101 MHz, CDCl 3 ) S24
25 1 H NMR for 1o (400 MHz, CDCl 3 ) 13 C NMR for 1o (101 MHz, CDCl 3 ) S25
26 1 H NMR for 1p (400 MHz, CDCl 3 ) 13 C NMR for 1p (101 MHz, CDCl 3 ) S26
27 19 F NMR for 1p (376 MHz, CDCl 3 ) 1 H NMR for 1q (400 MHz, CDCl 3 ) S27
28 13 C NMR for 1q (101 MHz, CDCl 3 ) 1 H NMR for 1r (400 MHz, CDCl 3 ) S28
29 13 C NMR for 1r (101 MHz, CDCl 3 ) 1 H NMR for 1s (400 MHz, CDCl 3 ) S29
30 13 C NMR for 1s (101 MHz, CDCl 3 ) 1 H NMR for 1t (400 MHz, CDCl 3 ) S30
31 13 C NMR for 1t (101 MHz, CDCl 3 ) 1 H NMR for 1u (400 MHz, CDCl 3 ) S31
32 13 C NMR for 1u (101 MHz, CDCl 3 ) 1 H NMR for 1v (400 MHz, CDCl 3 ) S32
33 13 C NMR for 1v (101 MHz, CDCl 3 ) 1 H NMR for 1w (400 MHz, CDCl 3 ) S33
34 13 C NMR for 1w (101 MHz, CDCl 3 ) 1 H NMR for 1x (400 MHz, CDCl 3 ) S34
35 13 C NMR for 1x (101 MHz, CDCl 3 ) 1 H NMR for 1y (400 MHz, CDCl 3 ) S35
36 13 C NMR for 1y (101 MHz, CDCl 3 ) 1 H NMR for 1z (400 MHz, CDCl 3 ) S36
37 13 C NMR for 1z (101 MHz, CDCl 3 ) 1 H NMR for 1aa (400 MHz, CDCl 3 ) S37
38 13 C NMR for 1aa (101 MHz, CDCl 3 ) 1 H NMR for 1ab (400 MHz, CDCl 3 ) S38
39 13 C NMR for 1ab (101 MHz, CDCl 3 ) 1 H NMR for 1ac (400 MHz, CDCl 3 ) S39
40 13 C NMR for 1ac (101 MHz, CDCl 3 ) 1 H NMR for 2b (400 MHz, CDCl 3 ) S40
41 19 F NMR for 2b (376 MHz, CDCl 3 ) 1 H NMR for 2c (400 MHz, CDCl 3 ) S41
42 19 F NMR for 2c (376 MHz, CDCl 3 ) 1 H NMR for 2d (400 MHz, CDCl 3 ) S42
43 19 F NMR for 2d (376 MHz, CDCl 3 ) 1 H NMR for 2e (400 MHz, CDCl 3 ) S43
44 19 F NMR for 2e (376 MHz, CDCl 3 ) 1 H NMR for 2f (400 MHz, CDCl 3 ) S44
45 19 F NMR for 2f (376 MHz, CDCl 3 ) 1 H NMR for 2g (400 MHz, CDCl 3 ) S45
46 19 F NMR for 2g (376 MHz, CDCl 3 ) 1 H NMR for 2h (400 MHz, CDCl 3 ) S46
47 19 F NMR for 2h (376 MHz, CDCl 3 ) 1 H NMR for 3a (400 MHz, CDCl 3 ) S47
48 13 C NMR for 3a (101 MHz, CDCl 3 ) 13 C NMR DEPT 135 for 3a (101 MHz, CDCl 3 ) S48
49 13 C NMR DEPT 90 for 3a (101 MHz, CDCl 3 ) 13 C NMR DEPT 45 for 3a (101 MHz, CDCl 3 ) S49
50 19 F NMR for 3a (376 MHz, CDCl 3 ) 1 H NMR for 3b (400 MHz, CDCl 3 ) S50
51 13 C NMR for 3b (101 MHz, CDCl 3 ) 19 F NMR for 3b (376 MHz, CDCl 3 ) S51
52 1 H NMR for 3c (400 MHz, CDCl 3 ) 13 C NMR for 3c (101 MHz, CDCl 3 ) S52
53 19 F NMR for 3c (376 MHz, CDCl 3 ) 1 H NMR for 3d (400 MHz, CDCl 3 ) S53
54 13 C NMR for 3d (101 MHz, CDCl 3 ) 19 F NMR for 3d (376 MHz, CDCl 3 ) S54
55 1 H NMR for 3e (400 MHz, CDCl 3 ) 13 C NMR for 3e (101 MHz, CDCl 3 ) S55
56 19 F NMR for 3e (376 MHz, CDCl 3 ) 1 H NMR for 3f (400 MHz, CDCl 3 ) S56
57 13 C NMR for 3f (101 MHz, CDCl 3 ) 19 F NMR for 3f (376 MHz, CDCl 3 ) S57
58 1 H NMR for 3g (400 MHz, CDCl 3 ) 13 C NMR for 3g (101 MHz, CDCl 3 ) S58
59 19 F NMR for 3g (376 MHz, CDCl 3 ) 1 H NMR for 3h (400 MHz, CDCl 3 ) S59
60 13 C NMR for 3h (101 MHz, CDCl 3 ) 19 F NMR for 3h (376 MHz, CDCl 3 ) S60
61 1 H NMR for 3i (400 MHz, CDCl 3 ) 13 C NMR for 3i (101 MHz, CDCl 3 ) S61
62 19 F NMR for 3i (376 MHz, CDCl 3 ) 1 H NMR for 3j (400 MHz, CDCl 3 ) S62
63 13 C NMR for 3j (101 MHz, CDCl 3 ) 19 F NMR for 3j (376 MHz, CDCl 3 ) S63
64 1 H NMR for 3k (400 MHz, CDCl 3 ) 13 C NMR for 3k (101 MHz, CDCl 3 ) S64
65 19 F NMR for 3k (376 MHz, CDCl 3 ) 1 H NMR for 3l (400 MHz, CDCl 3 ) S65
66 13 C NMR for 3l (101 MHz, CDCl 3 ) 19 F NMR for 3l (376 MHz, CDCl 3 ) S66
67 1 H NMR for 3m (400 MHz, CDCl 3 ) 13 C NMR for 3m (101 MHz, CDCl 3 ) S67
68 19 F NMR for 3m (376 MHz, CDCl 3 ) 1 H NMR for 3n (400 MHz, CDCl 3 ) S68
69 13 C NMR for 3n (101 MHz, CDCl 3 ) 19 F NMR for 3n (376 MHz, CDCl 3 ) S69
70 1 H NMR for 3o (400 MHz, CDCl 3 ) 13 C NMR for 3o (101 MHz, CDCl 3 ) S70
71 19 F NMR for 3o (376 MHz, CDCl 3 ) 1 H NMR for 3p (400 MHz, CDCl 3 ) S71
72 13 C NMR for 3p (101 MHz, CDCl 3 ) 19 F NMR for 3p (376 MHz, CDCl 3 ) S72
73 1 H NMR for 3q (400 MHz, CDCl 3 ) 13 C NMR for 3q (101 MHz, CDCl 3 ) S73
74 19 F NMR for 3q (376 MHz, CDCl 3 ) 1 H NMR for 3r (400 MHz, CDCl 3 ) S74
75 13 C NMR for 3r (101 MHz, CDCl 3 ) 19 F NMR for 3r (376 MHz, CDCl 3 ) S75
76 1 H NMR for 3s (400 MHz, CDCl 3 ) 13 C NMR for 3s (101 MHz, CDCl 3 ) S76
77 19 F NMR for 3s (376 MHz, CDCl 3 ) 1 H NMR for 3t (400 MHz, CDCl 3 ) S77
78 13 C NMR for 3t (101 MHz, CDCl 3 ) 19 F NMR for 3t (376 MHz, CDCl 3 ) S78
79 1 H NMR for 3u (400 MHz, CDCl 3 ) 13 C NMR for 3u (101 MHz, CDCl 3 ) S79
80 19 F NMR for 3u (376 MHz, CDCl 3 ) 1 H NMR for 3v (400 MHz, CDCl 3 ) S80
81 13 C NMR for 3v (101 MHz, CDCl 3 ) 19 F NMR for 3v (376 MHz, CDCl 3 ) S81
82 1 H NMR for 3w (400 MHz, CDCl 3 ) 13 C NMR for 3w (101 MHz, CDCl 3 ) S82
83 19 F NMR for 3w (376 MHz, CDCl 3 ) 1 H NMR for 3x (400 MHz, CDCl 3 ) S83
84 13 C NMR for 3x (101 MHz, CDCl 3 ) 19 F NMR for 3x (376 MHz, CDCl 3 ) S84
85 1 H NMR for 3y (400 MHz, CDCl 3 ) 13 C NMR for 3y (101 MHz, CDCl 3 ) S85
86 19 F NMR for 3y (376 MHz, CDCl 3 ) 1 H NMR for 3z (400 MHz, CDCl 3 ) S86
87 13 C NMR for 3z (101 MHz, CDCl 3 ) 19 F NMR for 3z (376 MHz, CDCl 3 ) S87
88 1 H NMR for 3aa (400 MHz, CDCl 3 ) 13 C NMR for 3aa (101 MHz, CDCl 3 ) S88
89 19 F NMR for 3aa (376 MHz, CDCl 3 ) 1 H NMR for 3ab (400 MHz, CDCl 3 ) S89
90 13 C NMR for 3ab (101 MHz, CDCl 3 ) 19 F NMR for 3ab (376 MHz, CDCl 3 ) S90
91 1 H NMR for 3ac (400 MHz, CDCl 3 ) 13 C NMR for 3ac (101 MHz, CDCl 3 ) S91
92 19 F NMR for 3ac (376 MHz, CDCl 3 ) 1 H NMR for 3ad (400 MHz, CDCl 3 ) S92
93 13 C NMR for 3ad (101 MHz, CDCl 3 ) 19 F NMR for 3ad (376 MHz, CDCl 3 ) S93
94 1 H NMR for 3ae (400 MHz, CDCl 3 ) 13 C NMR for 3ae (101 MHz, CDCl 3 ) S94
95 19 F NMR for 3ae (376 MHz, CDCl 3 ) 1 H NMR for 3af (400 MHz, CDCl 3 ) S95
96 13 C NMR for 3af (101 MHz, CDCl 3 ) 19 F NMR for 3af (376 MHz, CDCl 3 ) S96
97 1 H NMR for 3ag (400 MHz, CDCl 3 ) 13 C NMR for 3ag (101 MHz, CDCl 3 ) S97
98 19 F NMR for 3ag (376 MHz, CDCl 3 ) 1 H NMR for 3ah (400 MHz, CDCl 3 ) S98
99 13 C NMR for 3ah (101 MHz, CDCl 3 ) 19 F NMR for 3ah (376 MHz, CDCl 3 ) S99
100 1 H NMR for 3ai (400 MHz, CDCl 3 ) 13 C NMR for 3ai (101 MHz, CDCl 3 ) S100
101 19 F NMR for 3ai (376 MHz, CDCl 3 ) 1 H NMR for 3aj (400 MHz, CDCl 3 ) S101
102 13 C NMR for 3aj (101 MHz, CDCl 3 ) 19 F NMR for 3aj (376 MHz, CDCl 3 ) S102
103 1 H NMR for 3ak (400 MHz, CDCl 3 ) 13 C NMR for 3ak (101 MHz, CDCl 3 ) S103
104 19 F NMR for 3ak (376 MHz, CDCl 3 ) 31 P NMR for 3ak (162 MHz, CDCl 3 ) S104
105 1 H NMR for 4 (400 MHz, CDCl 3 ) 13 C NMR for 4 (101 MHz, CDCl 3 ) S105
106 19 F NMR for 4 (376 MHz, CDCl 3 ) 1 H NMR for 5 (400 MHz, CDCl 3 ) S106
107 13 C NMR for 5 (101 MHz, CDCl 3 ) 19 F NMR for 5 (376 MHz, CDCl 3 ) S107
108 1 H NMR for 6 (400 MHz, CDCl 3 ) 19 F NMR for 6 (376 MHz, CDCl 3 ) S108
109 1 H NMR for 7 (400 MHz, CDCl 3 ) 19 F NMR for 7 (376 MHz, CDCl 3 ) S109
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