Supporting Information for
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- Γερβάσιος Κορομηλάς
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1 Supporting Information for Palladium-Catalyzed C-H Bond Functionalization of C6-Arylpurines Hai-Ming Guo,* Wei-Hao Rao, Hong-Ying iu, Li-Li Jiang, Ge ng, Jia-Jia Jin, Xi-ing Yang, and Gui-Rong Qu* College of Chemistry and Environmental Science, Key Laboratory of Green Chemical dia and Reactions of Ministry of Education, Henan ormal University, Xinxiang, , China; and School of Chemistry and Chemical Engineering, Henan Institute of Science and Technology, Xinxiang , China General Information...S1 Synthesis of Starting Materials...S2 General procedure...s3 Characterization of compounds...s4 References...S10 Copies of 1 H and 13 C MR spectra...s11 General Information: MR spectra were recorded with a 400 MHz spectrometer for 1 H MR, 100 MHz for 13 C MR. Chemical shifts δ are given in ppm relative to the residual proton signals of the deuterated solvent CD 3 for 1 H and 13 C MR. High resolution mass spectra were taken with a 3000 mass spectrometer, using Waters Q-TofMS/MS system. For column chromatography silica gel ( mesh) was used as the stationary phase. All reactions were monitored by thin layer chromatography (TLC). All regents and solvents were purchased from commercial sources and purified commonly before used. S1
2 Synthesis of Starting Materials Starting materials 1a-i 1, 1l 1, 1j 2 and 1k 1, 3 were synthesized according to the corresponding reference. AcO O 1a 1b 1c 1d H 3 C CH 3 HAc 1e 1f 1g 1h O 1i O 1j 1k 1l S2
3 General procedure for the purine-directed Pd-catalyzed C Ar -H bonds acetoxylation In a 35 ml tube containing a stir bar, C6-aryl purine (1a-1j) or 1l (0.3 mmol), Pd() 2 (33 mg, mmol), PhI() 2 (0.144 mg, 0.45 mmol) were dissolved in Ac 2 O (1 ml) and AcOH (1 ml). The tube was sealed with a Teflon lined cap and the reaction mixture was stirred at 120 o C for 3-15 h until TLC showed the reaction almost proceeded completely. The resulting mixture was cooled to room temperature. The solvent was removed by distillation under vacuum and the residue was purified by column chromatography on silica gel (eluent: petroleum ether/et) to afford the corresponding acetoxylated product. General procedure for the purine-directed diverse C-H bond functionalizations In a 35 ml tube containing a stir bar, 1c or 1g, 1i, 1l (0.3 mmol), Pd() 2 (33 mg, mmol), PhI() 2 ( mg, 0.45 mmol) or BS (0.45 mmol), CS (0.45 mmol) were dissolved in solvent as indicated in Table 3. The tube was sealed with a Teflon lined cap and the reaction mixture was stirred at 100 o C for 3-15 h until TLC showed the reaction almost proceeded completely. The resulting mixture was cooled to room temperature. The solvent was removed by distillation under vacuum and the residue was purified by column chromatography on silica gel (eluent: petroleum ether/et) to afford the corresponding product. S3
4 Characterization of compounds Acetic acid 2-(9-benzyl-9H-purin-6-yl)-phenyl ester (2a) 1 H MR (400 MHz, CD 3 ) δ 9.05 (s, 1H), (m, 1H), 8.07 (s, 1H), (m, 1H), (m, 7H), 5.47 (s, 2H), 2.19 (s, 3H); 13 C MR (100 MHz, CD 3 ) δ 169.6, 154.5, 152.3, 152.2, 148.8, 144.4, 135.1, 132.5, 131.7, 131.3, 129.2, 128.6, 128.0, 127.8, 126.1, 123.9, 47.3, 21.3; HRMS: calcd for C 20 H 16 4 ao 2 [M + a] , found Acetic acid 2-(9-isopropyl-9H-purin-6-yl)-phenyl ester (2b) 1 H MR (400 MHz, CD 3 ) δ 9.00 (s, 1H), 8.18 (dd, J = 8.0, 1.2 Hz, 1H), 8.16 (s, 1H), 7.53 (t, J = 1.2 Hz, 1H), 7.43 (td, J = 7.2, 0.8 Hz, 1H), 7.28 (d, J = 0.8 Hz, 1H), 4.97 (quint, J = 6.8 Hz, 1H), 2.19 (s, 1H), 1.68 (d, J = 6.8 Hz, 6H); 13 C MR (100 MHz, CD 3 ) δ 169.6, 154.4, 151.7, 148.8, 142.3, 132.5, 132.3, 131.1, 128.1, 126.0, 123.9, 47.4, 22.5, 21.2; HRMS: calcd for C 16 H 16 4 ao 2 [M + a] , found Acetic acid 2-(9-butyl-9H-purin-6-yl)-phenyl ester (2c) 1 H MR (400 MHz, CD 3 ) δ 9.03 (s,1h), 8.20 (d, J = 7.6 Hz, 1H), 8.09 (s, 1H), 7.54 (t, J = 7.6 Hz, 1H), 7.43 (t, J = 7.6 Hz, 1H), 7.28 (d, J = 8.4 Hz, 1H), 4.32 (t, J = 7.2 Hz, 2H), 2.20 (s, 3H), (m, 2H), (m, 2H), (m, 3H). 13 C MR (100 MHz, CD 3 ) δ 169.6, 152.0, 148.8, 132.4, 131.2, 126.1, 123.9, 43.8, 31.9, 21.2, 19.9, 13.5; HRMS: calcd for C 17 H 18 4 ao 2 [M + a] , found S4
5 (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(6-(2-acetoxyphenyl)-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate (2da) AcO O 1 H MR (400 MHz, CD 3 ) δ 9.03 (s, 1H), 8.25 (s, 1H), 8.15 (dd, J = 7.6, 1.2 Hz, 1H), (m, 1H), 7.43 (t, J = 7.6 Hz, 1H), 7.28 (d, J = 8.0 Hz, 1H), 6.27 (d, J = 5.2 Hz, 1H), 6.01 (t, J = 5.2 Hz, 1H), 5.71 (t, J = 5.2 Hz, 1H), (m, 3H), 2.18 (s, 3H), 2.16 (s, 3H), 2.12 (s, 3H), 2.10 (s, 3H); 13 C MR (100 MHz, CD 3 ) δ 170.3, 169.6, 169.4, 155.1, 152.4, 151.6, 148.8, 142.9, 132.5, 131.5, 127.7, 126.1, 123.9, 86.5, 80.4, 73.0, 70.6, 63.0, 21.2, 20.7, 20.5, 20.4; HRMS: calcd for C 24 H 24 4 ao 9 [M + a] , found (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(6-(2,6-diacetoxyphenyl)-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate (2db) AcO AcO O 1 H MR (400 MHz, CD 3 ) δ 9.05 (s, 1H), 8.22 (s, 1H), 7.55 (t, J = 8.4 Hz, 1H), 7.24 (d, J = 8.4 Hz, 2H), 6.24 (d, J = 5.2 Hz, 1H), 5.97 (t, J = 5.2 Hz, 1H), 5.72 (t, J = 5.2 Hz, 1H), (m, 3H), 2.17 (s, 3H), 2.11 (s, 3H), 2.10 (s, 3H), 2.01 (s, 6H); 13 C MR (100 MHz, CD 3 ) δ 170.3, 169.6, 169.4, 168.7, 152.3, 152.1, 151.2, 149.3, 143.3, 133.7, 130.7, 121.4, 120.9, 86.8, 80.3, 73.1, 70.5, 62.9, 20.9, 20.7, 20.5, 20.4; HRMS: calcd for C 26 H 26 4 ao 11 [M + a] , found Acetic acid 2-(2-chloro-9-butyl-9H-purin-6-yl)-phenyl ester (2e) 1 H MR (400 MHz, CD 3 ) δ 8.37 (dd, J = 8.0, 1.2 Hz, 1H), 8.07 (s, 1H), (m, 1H), (m, 1H), 7.26 (d, J = 7.6 Hz, 1H), 4.27 (t, J = 7.2 Hz, 2H), 2.30 (s, 3H), (m, 2H), (m, 2H), 0.98 (t, J = 7.2 Hz, 3H); 13 C MR (100 MHz, CD 3 ) δ 169.8, 155.8, 153.9, 153.6, 149.1, 145.2, 132.9, 131.9, 130.7, 126.8, 126.1, 124.2, 43.9, 31.8, 21.2, 19.9, 13.5; HRMS: calcd for C 17 H 17 4 ao 2 [M + S5
6 a] , found Acetic acid 2-(2-acetylamino-9-butyl-9H-purin-6-yl)-4-methyl-phenyl ester (2f) 1 H MR (400 MHz, CD 3 ) δ 8.25 (br, 1H), 7.97 (s, 1H), 7.77 (d, J = 2.0 Hz, 1H), 7.32 (dd, J = 8.4, 1.6 Hz, 1H), 7.14 (d, J = 8.0 Hz, 1H), 4.22 (t, J = 7.2 Hz, 2H), 2.59 (s, 3H), 2.42 (s, 3H), 2.11 (s, 3H), (m, 2H), (m, 2H), 0.98 (t, J = 7.2 Hz, 3H); 13 C MR (100 MHz, CD 3 ) δ 169.5, 155.6, 152.9, 152.4, 146.4, 144.1, 135.8, 132.3, 132.0, 128.5, 127.5, 123.4, 43.6, 31.7, 25.1, 21.2, 20.9, 19.9, 13.5; HRMS: calcd for C 20 H 23 5 ao 3 [M + a] , found Acetic acid 2-(9-butyl-9H-purin-6-yl)-4-methyl-phenyl ester (2g) 1 H MR (400 MHz, CD 3 ) δ 9.00 (s, 1H), 8.08 (s, 1H), 7.93 (s, 1H), 7.32 (dd, J = 8.0, 2.0 Hz, 1H), 7.15 (d, J = 8.0 Hz, 1H), 4.29 (t, J = 7.2 Hz, 2H), 2.43 (s, 3H), 2.13 (s, 3H), (m, 2H), (m, 2H), 0.97 (t, J = 7.2 Hz, 3H); 13 C MR (100 MHz, CD 3 ) δ 169.7, 154.5, 152.0, 152.0, 146.6, 144.6, 135.7, 132.6, 131.9, 131.8, 127.7, 123.5, 43.8, 31.9, 21.3, 21.0, 19.9, 13.5; HRMS: calcd for C 18 H 21 4 O 2 [M + H] , found Acetic acid 2-(9-benzyl-9H-purin-6-yl)-5-methyl-phenyl ester (2h) CH 3 1 H MR (400 MHz, CD 3 ) δ 9.03 (s, 1H), 8.15 (d, J = 8.0 Hz, 1H), 8.07 (s, 1H), (m, 5H), 7.23 (d, J = 8.0 Hz, 1H), 7.08 (s, 1H), 5.47 (s, 2H), 2.44 (s, 3H), 2.19 (s, 3H); 13 C MR (100 MHz, CD 3 ) δ 169.8, 154.6, 152.2, 152.1, 148.7, 144.3, 142.2, 135.1, 132.4, 131.5, 129.4, 128.6, 127.8, 126.9, 125.0, 124.4, 47.3, 21.4, 21.3; HRMS: calcd for C 21 H 18 4 ao 2 [M + a] , found S6
7 Acetic acid 2-(9-butyl-9H-purin-6-yl)-4-methoxy-phenyl ester (2i) H 3 CO 1 H MR (400 MHz, CD 3 ) δ 9.01 (s, 1H), 8.08 (s, 1H), 7.73 (d, J = 3.2 Hz, 1H), 7.18 (d, J = 8.8 Hz, 1H), 7.05 (dd, J = 8.8, 3.2 Hz, 1H), 4.31 (t, J = 7.2 Hz, 2H), 3.87 (s, 3H), 2.14 (s, 3H), (m, 2H), (m, 2H), 0.98 (t, J = 7.2 Hz, 3H); 13 C MR (100 MHz, CD 3 ) δ 169.9, 157.1, 154.2, 152.1, 151.9, 144.6, 142.3, 131.8, 128.6, 124.6, 117.1, 116.7, 55.7, 43.8, 31.9, 21.2, 19.9, 13.5; HRMS: calcd for C 18 H 20 4 ao 3 [M + a] , found Acetic acid 2-(9-benzyl-9H-purin-6-yloxy)-phenyl ester (2j) O 1 H MR (400 MHz, CD 3 ) δ 8.54 (s, 1H), 8.00 (s, 1H), (m, 9H), 5.46 (s, 2H), 2.03 (s, 3H); 13 C MR (100 MHz, CD 3 ) δ 168.3, 159.3, 153.3, 152.2, 143.7, 143.1, 142.6, 134.9, 129.2, 128.7, 127.9, 126.6, 126.5, 123.8, 123.7, 121.1, 47.7, HRMS: calcd for C 20 H 17 4 O 3 [M + H] , found Acetic acid 2-(9-benzyl-6-methyl-9H-purin-2-yl)-phenyl ester (2k) CH 3 1 H MR (400 MHz, CD 3 ) δ 8.22 (dd, J = 7.6, 1.6 Hz, 1H), 7.99 (s, 1H), (m, 1H), (m, 4H), (m, 2H), 7.16 (d, J = 8.0 Hz, 1H), 5.46 (s, 2H), 2.90 (s, 3H), 2.21 (s, 3H); 13 C MR (100 MHz, CD 3 ) δ 169.8, 158.9, 157.9, 149.0, 143.9, 135.9, 132.0, 131.4, 130.6, 129.1, 128.5, 127.8, 126.2, 123.7, 47.0, 21.2, 19.7; HRMS: calcd for C 21 H 18 4 ao 2 [M + a] , found butyl-6-(2-methoxy-phenyl)-9H-purine (3a) O S7
8 1 H MR (400 MHz, CD 3 ) δ 9.06 (s, 1H), 8.05 (s, 1H), 7.65 (dd, J = 7.6, 1.6 Hz, 1H), 7.47 (td, J = 8.4, 1.6 Hz, 1H), (m, 2H), 4.31 (t, J = 7.2 Hz, 2H), 3.84 (s, 3H), (m, 2H), (m, 2H), 0.99 (t, J = 7.2 Hz, 3H); 13 C MR (100 MHz, CD 3 ) δ 157.5, 156.5, 152.2, 151.7, 144.3, 132.6, 131.7, 131.3, 124.9, 120.7, 111.9, 55.9, 43.7, 31.9, 19.9, 13.5; HRMS: calcd for C 16 H 19 4 O [M + H] , found (2-Ethoxy-phenyl)-9-butyl-9H-purine (3b) OEt 1 H MR (400 MHz, CD 3 ) δ 9.04 (s, 1H), 8.05 (s, 1H), 7.64 (dd, J = 7.6, 1.2 Hz, 1H), (m, 1H), (m, 2H), 4.31 (t, J = 7.2 Hz, 2H), 4.10 (q, J = 7.2 Hz, 2H), (m, 2H), (m, 2H), 1.22 (t, J = 7.2 Hz, 3H), 0.98 (t, J = 7.2 Hz, 3H); 13 C MR (100 MHz, CD 3 ) δ 156.9, 156.7, 152.2, 151.5, 144.0, 132.5, 131.5, 131.2, 125.2, 120.6, 113.0, 64.3, 43.7, 31.9, 19.9, 14.7, 13.5; HRMS: calcd for C 17 H 21 4 O [M + H] , found (2-bromophenyl)-9-butyl-9H-purine (3c) Br 1 H MR (400 MHz, CD 3 ) δ 9.09 (s, 1H), 8.11 (s, 1H), 7.76 (d, J = 8.0 Hz, 1H), 7.63 (d, J = 8.0 Hz, 1H), 7.47 (t, J = 7.6 Hz, 1H), (m, 1H), 4.34 (t, J = 7.2 Hz, 2H), (m, 2H), (m, 2H), (t, J = 7.2 Hz, 3H); 13 C MR (100 MHz, CD 3 ) δ 157.2, 152.1, 152.0, 144.9, 136.5, 133.6, 132.0, 131.7, 130.9, 127.4, 122.0, 43.9, 31.9, 19.9, 13.5; HRMS: calcd for C 15 H 15 Br 4 a [M + a] , found (2-chlorophenyl)-9-butyl-9H-purine (3d) 1 H MR (400 MHz, CD 3 ) δ 9.08 (s, 1H), 8.10 (s, 1H), (m, 1H), (m, 1H), S8
9 (m, 2H), 4.32 (t, J = 7.2 Hz, 2H), (m, 2H), (m, 2H), 0.98 (t, J = 7.2 Hz, 3H); 13 C MR (100 MHz, CD 3 ) δ 156.0, 152.2, 151.9, 144.9, 134.6, 132.9, 132.3, 131.7, 130.8, 130.4, 126.8, 43.8, 31.9, 19.9, 13.5; HRMS: calcd for C 15 H 15 4 a [M + a ] , found (2-chloro-5-methylphenyl)-9-butyl-9H-purine (3e) 1 H MR (400 MHz, CD 3 ) δ 9.07 (s, 1H), 8.10 (s, 1H), 7.45 (d, J = 1.6 Hz, 1H), 7.42 (d, J = 8.0 Hz, 1H), 7.23 (dd, J = 8.4, 1.6 Hz, 1H), 4.32 (t, J = 7.2 Hz, 2H), 2.38 (s, 3H), (m, 2H), (m, 2H), 0.98 (t, J = 7.2 Hz, 3H); 13 C MR (100M Hz, CD 3 ) δ 156.3, 152.2, 151.9, 144.9, 136.8, 134.3, 132.3, 132.1, 131.6, 130.1, 129.9, 43.8, 31.9, 20.9, 19.9, 13.5; HRMS: calcd for C 16 H 18 4 [M + H ] , found (2-chloro-5-methoxyphenyl)-9-butyl-9H-purine (3f) O 1 H MR (400 MHz, CD 3 ) δ 9.08 (s, 1H), 8.11 (s, 1H), 7.44 (d, J = 8.8 Hz, 1H), 7.17 (d, J = 3.2 Hz, 1H), 6.98 (dd, J = 8.8, 3.2 Hz, 1H), 4.32 (t, J = 7.2 Hz, 2H), 3.82 (s, 3H), (m, 2H), (m, 2H), 0.99 (t, J = 7.2 Hz, 3H); 13 C MR (100 MHz, CD 3 ) δ 158.2, 155.9, 152.2, 151.9, 145.0, 135.2, 132.2, 131.2, 124.3, 117.1, 116.5, 55.6, 43.8, 31.9, 19.9, 13.5; HRMS: calcd for C 16 H 18 4 O [M + H ] , found (2-chloro-4-methylphenyl)-9-butyl-9H-purine (3g) 1 H MR (400 MHz, CD 3 ) δ 9.07 (s, 1H), 8.08 (s, 1H), 7.57 (d, J = 8.0 Hz, 1H), 7.38 (s, 1H), 7.22 (d, J = S9
10 8.0 Hz, 1H), 4.31 (t, J = 7.2 Hz, 2H), 2.40 (s, 3H), (m, 2H), (m, 2H), 0.98 (t, J = 7.2 Hz, 3H); 13 C MR (100 MHz, CD 3 ) δ 156.2, 152.2, 151.9, 144.8, 141.3, 132.6, 132.3, 131.6, 131.6, 130.9, 127.7, 43.8, 31.9, 21.1, 19.9, 13.5; HRMS: calcd for C 16 H 18 4 [M + H ] , found References: 1. a) I. Černǎ, R. Pohl, B. Klepetářová and M. Hocek, J. Org. Chem., 2008, 73, 9048; b) M. K. Lakshman, J. H. Hilmer, J. Q. Martin, J. C. Keeler, Y. Q. V. Dinh, F.. gassa and L.;M. Russon, J. Am. Chem. Soc., 2001, 123, L.-K. Huang, Y.-C. Cherng, Y.-R. Cheng, J.-P. Jang, Y.-L. Chao and Y.-J. Cherng, Tetrahedron, 2007, 63, G. R. Qu, Z. J. Mao, H. Y. iu, D. C. Wang, C. Xia and H. M. Guo, Org. Lett., 2009, 11, S10
11 Copies of 1 H and 13 C MR spectra a ppm (f1) a 200 ppm (f1) S11
12 b ppm (f1) b ppm (f1) S12
13 c ppm (f1) c 200 ppm (f1) S13
14 AcO O 2da ppm (f1) AcO O 2da 200 ppm (f1) S14
15 AcO AcO O 2db ppm (f1) AcO AcO O 2db 200 ppm (f1) S15
16 e ppm e ppm S16
17 H 3 C 2f HAc ppm (f1) H 3 C 2f HAc 200 ppm (f1) S17
18 g ppm (t1) g 200 ppm (t1) S18
19 CH 3 2h ppm (t1) CH 3 2h 200 ppm (t1) S19
20 O 2i ppm (t1) O 2i 200 ppm (t1) S20
21 H1 Solvent:CD3 o:01 rwh O 2j ppm C13 Solvent:CD3 o:01 rwh O 2j ppm S21
22 1H Solvent:CD3 o:04 rwh CH 3 2k ppm C Solvent:CD3 o:02 rwh CH 3 2k ppm S22
23 H1 Solvent:CD3 o:02 rwh O 3a ppm C13 Solvent:CD3 o:02 rwh O 3a ppm S23
24 1H Solvent:CD3 o:07 rwh OEt 3b ppm OEt 3b ppm S24
25 1H Solvent:CD3 o:05 rwh Br 3c ppm C Solvent:CD3 o:23(01) rwh Br 3c ppm S25
26 1H Solvent:CD3 o:04 rwh d ppm C Solvent:CD3 o:01 rwh d ppm S26
27 e ppm (t1) e ppm (t1) S27
28 O 3f ppm (t1) O 3f 200 ppm (t1) S28
29 g ppm (t1) g ppm (t1) S29
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