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1 Supporting Information Nucleophilic ipso-substitution of Aryl Methyl Ethers through Aryl C OMe Bond Cleavage; an Access to Functionalized Bisthiophenes Abhishek Kumar Mishra, Ajay Verma, and Srijit Biswas*, Division of Molecular Synthesis and Drug Discovery, Centre of Bio-Medical Research, SGPGIMS Campus, Raebareli Road, Lucknow , India Division of NMR and Metabolomics, Centre of Bio-Medical Research, SGPGIMS Campus, Raebareli Road, Lucknow , India * srijit.biswas@cbmr.res.in; srijit_biswas@yahoo.co.in S1
2 Contents Page No. 1. Checklist of characterization data of all compounds S3 S5 2. Copies of 1 H and 13 C NMR spectra of all products S6 S36 3. Copies of 1 H NMR spectra of Deuterated Compounds S37 S38 4. Copies of 2-D NMR spectra of 4a 4e, and 6b S39 S46 5. Kinetic experiments S47 S59 6. References and Notes S60 S2
3 1. Checklist of characterization data of all products: Entry Compounds Known / Unknown 1 H NMR 13 C NMR HRMS 1 Known 2 3b O 6 Known 3 Unknown 4 Known 5 Known 6 3f H N Known 7 Known 8 Known 9 Known 10 Unknown S3
4 11 Known 12 Known 13 Known 14 Unknown 15 Known 16 Known 17 Unknown 18 Unknown 19 Unknown 20 S O 5 4a S Unknown 21 Unknown S4
5 22 Unknown 23 S HN 4d S OMe Unknown 24 Unknown 25 Known 26 Known 27 Unknown 28 Unknown 29 Known 30 Known 31 Unknown S5
6 2. Copies of 1 H and 13 C NMR spectra of all products: 3a- 1 H NMR (CDCl 3, 400 MHz) 3a- 13 C NMR (CDCl 3, 100 MHz) S6
7 3b- 1 H NMR (CDCl 3, 400 MHz) 3b- 13 C NMR (CDCl 3, 100 MHz) S7
8 3c- 1 H NMR (CDCl 3, 400 MHz) 3c- 13 C NMR (CDCl 3, 100 MHz) S8
9 3d- 1 H NMR (CDCl 3, 400 MHz) 3d- 13 C NMR (CDCl 3, 100 MHz) S9
10 3e- 1 H NMR (CDCl 3, 400 MHz) 3e- 13 C NMR (CDCl 3, 100 MHz) S10
11 3f- 1 H NMR (CDCl 3, 400 MHz) 3f- 13 C NMR (CDCl 3, 100 MHz) S11
12 3g- 1 H NMR (CDCl 3, 400 MHz) 3g- 13 C NMR (CDCl 3, 100 MHz) S12
13 3h- 1 H NMR (CDCl 3, 400 MHz) 3h- 13 C NMR (CDCl 3, 100 MHz) S13
14 3i- 1 H NMR (CDCl 3, 400 MHz) 3i- 13 C NMR (CDCl 3, 100 MHz) S14
15 3j- 1 H NMR (CDCl 3, 400 MHz) 3j- 13 C NMR (CDCl 3, 100 MHz) S15
16 3k- 1 H NMR (CDCl 3, 400 MHz) 3k- 13 C NMR (CDCl 3, 100 MHz) S16
17 3l- 1 H NMR (CDCl 3, 400 MHz) 3l- 13 C NMR (CDCl 3, 100 MHz) S17
18 3m- 1 H NMR (CDCl 3, 400 MHz) 3m- 13 C NMR (CDCl 3, 100 MHz) S18
19 3n- 1 H NMR (CDCl 3, 400 MHz) 3n- 13 C NMR (CDCl 3, 100 MHz) S19
20 3o- 1 H NMR (CDCl 3, 400 MHz) 3o- 13 C NMR (CDCl 3, 100 MHz) S20
21 3p- 1 H NMR (CDCl 3, 400 MHz) 3p- 13 C NMR (CDCl 3, 100 MHz) S21
22 3q- 1 H NMR (CDCl 3, 800 MHz) 3q- 13 C NMR (CDCl 3, 200 MHz) S22
23 3r- 1 H NMR (CDCl 3, 800 MHz) 3r- 13 C NMR (CDCl 3, 200 MHz) S23
24 3s- 1 H NMR (CDCl 3, 800 MHz) 3s- 13 C NMR (CDCl 3, 200 MHz) S24
25 4a- 1 H NMR (CDCl 3, 400 MHz) 4a- 13 C NMR (CDCl 3, 100 MHz) S25
26 4b- 1 H NMR (CDCl 3, 400 MHz) 4b- 13 C NMR (CDCl 3, 100 MHz) S26
27 4c- 1 H NMR (CDCl 3, 400 MHz) 4c- 13 C NMR (CDCl 3, 100 MHz) S27
28 4d- 1 H NMR (CDCl 3, 400 MHz) 4d- 13 C NMR (CDCl 3, 100 MHz) S28
29 4e- 1 H NMR (CDCl 3, 400 MHz) 4e- 13 C NMR (CDCl 3, 100 MHz) S29
30 5a- 1 H NMR (CDCl 3, 400 MHz) 5a- 13 C NMR (CDCl 3, 100 MHz) S30
31 5b- 1 H NMR (CDCl 3, 400 MHz) 5b- 13 C NMR (CDCl 3, 100 MHz) S31
32 5c- 1 H NMR (CDCl 3, 400 MHz) 5c- 13 C NMR (CDCl 3, 100 MHz) S32
33 5d- 1 H NMR (CDCl 3, 400 MHz) 5d- 13 C NMR (CDCl 3, 100 MHz) S33
34 5e- 1 H NMR (CDCl 3, 400 MHz) 5e- 13 C NMR (CDCl 3, 100 MHz) S34
35 6a- 1 H NMR (CDCl 3, 400 MHz) 6a- 13 C NMR (CDCl 3, 100 MHz) S35
36 6b- 1 H NMR (CDCl 3, 400 MHz) 6b- 13 C NMR (CDCl 3, 100 MHz) S36
37 3. Copies of 1 H NMR spectra of Deuterated Compounds: 1a- 1 H NMR (CDCl 3, 400 MHz) 1a-D- 1 H NMR (CDCl 3, 400 MHz) S37
38 1e- 1 H NMR (CDCl 3, 400 MHz) 1e-D- 1 H NMR (CDCl 3, 400 MHz) S38
39 4. Copies of 2-D NMR spectra of 4a 4e, and 6b: 4a-NOESY (CDCl 3, 800 MHz, 300 K) S39
40 4b-NOESY (CDCl 3, 800 MHz, 300 K) S40
41 4c-NOESY (CDCl 3, 800 MHz, 300 K) S41
42 4c-HMBC (CDCl 3, 800 MHz, 300K) 1 S42
43 4c-HSQC (CDCl 3, 800 MHz, 300 K) S43
44 4d-NOESY (CDCl 3, 800 MHz, 300 K) S44
45 4e-NOESY (CDCl 3, 800 MHz, 300 K) S45
46 6b-NOESY (CDCl 3, 800 MHz, 300 K) S46
47 5. Kinetic experiments: General Methods: For kinetic experiments, reactions were set up in 2 mmol scale using the substrates 2- methoxynaphthalene (1a), 1-hexanol (2a) and TfOH catalyst in 3 ml dry toluene solvent at 120 C. An aliquot of 100 µl was taken out at a regular time-interval and directly placed in an NMR tube. 0.5 ml of CDCl 3 containing CH 2 Cl 2 (known amount) as internal standard was added. The integration ratios of CH 2 Cl 2 w.r.t 1a and 2a was set at t = 0 where no reaction took place. And the extent of product formations at different time intervals were monitored and calculated w.r.t the pre-determined integration of the internal standard CH 2 Cl 2 for each set of reactions. OMe Cat. TfOH O Toluene + HO 5+ MeOH 120 C 5 1a 2a 3a K-2 [1a : 2a : Catalyst = 2 mmol : 2 mmol : 20 mol%] S47
48 K-2 Time (min) [Nap-OHex] K-3 [1a : 2a : Catalyst = 4 mmol : 2 mmol : 20 mol%] K-3 [Nap-OHex] Time (min) mg/ml S48
49 K-4 [1a : 2a : Catalyst = 5 mmol: 2 mmol: 20 mol%] K-4 [Nap-OHex] Time (min) mg/ml S49
50 Graph between Rate of formation of Nap-OHex and the concentration of Nap-OHex [Nap-OHex] mg/ml Rate S50
51 K-2 [1a : 2a : Catalyst = 2 mmol : 2 mmol : 20 mol%] K-2 [Nap-OHex] Time (min) mg/ml S51
52 K-5 [1a : 2a : Catalyst = 2 mmol : 4 mmol : 20 mol%] K-5 [Nap-OHex] Time (min) mr/ml S52
53 K-6 [1a : 2a : Catalyst = 2 mmol: 5 mmol: 20 mol%] K-6 Time (min) [Nap-OHex] mg/ml S53
54 Graph between Rate of formation of Nap-OHex and the concentration of Hexanol [Hexanol] Rate [Nap-OHex] S54
55 K-10 [1a : 2a : Catalyst = 2 mmol: 2 mmol: 10 mol%] K-10 Time (min) [Nap-OHex] mg/ml S55
56 K-2 [1a : 2a : Catalyst = 2 mmol: 2 mmol: 20 mol%] K-2 [Nap-OHex] Time (min) mg/ml S56
57 K-7 [1a : 2b : Catalyst = 2 mmol: 2 mmol: 40 mol%] [Nap-OHex] Time (min) mg/ml S57
58 Graph between Rate of formation of Nap-OHex and the concentration of Catalyst: [Catalyst] Rate S58
59 Representative 1 H NMR for Kinetic Study: S59
60 6. References and Notes: (1) A gradient-selected magnitude mode HMBC spectrum was obtained with the following parameters: acquisition time = 249 ms in (F 2 ) and 25 ms in (F 1 ), Relaxation (d1) delay = 1.9 second, Number of Scan (NS) = 12, Dummy Scan (DS) = 16, complex data point = 1794 in F 2 and 1024 in F 1 dimension respectively, one bond proton-carbon heteronuclear coupling ( 1 J CH ) = 7 Hz, delay of evolution of long-range coupling (d6) = 70 ms. The spectra were processed with the following parameters: 4096 complex data point in F 2 and 2048 complex data point in F 1 dimension. Spectra were processed in magnitude mode with 90 degree sine bell shifted (SSB=2) window function. In HMBC (Heteronuclear Multiple Bond Correlation) spectrum long range correlation ( 2 J CH and 3 J CH ) between heteronuclear spins 1 H and 13 C occurs. S60
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