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1 SUPPRTING INFRMATIN Gold nanoparticles supported on Ti catalyse the cycloisomerisation/oxidative dimerisation of aryl propargyl ethers Christina Efe, Ioannis N. Lykakis, and Manolis Stratakis* Department of Chemistry, University of Crete, Voutes 00, Iraklion, Greece. Table of Contents Pages -: Synthesis and characterization of aryl propargyl ethers - and their cycloisomerisation products. Pages -: H and C NMR spectra of aryl propargyl ethers and their cycloisomerisation products. MS/HRMS copies of new compounds.
2 Experimental Section Nuclear magnetic resonance spectra were obtained on 00 and 00 MHz instruments. Isomeric purities were determined by H NMR and by GC analysis on a 0 meters HP- capillary column. All spectra reported herein were recorded in CDCl. Synthesis of propargyl aryl ethers - Propargyl aryl ethers - were prepared in yields ranging from -% by alkylation of the corresponding phenols with propargyl bromide or -bromo--butyne. In a typical example, equivalent of phenol was dissolved in dry DMF ( ml of solvent per mmol of phenol), and then. equivalents of Cs C were added. After minutes. equivalents of propargyl bromide (substrates -) or -bromo--butyne (substrates -) were added at ambient temperature. The reaction was monitored by TLC and after completion (- h), the mixture was diluted with ether and washed at least times with brine, to completely remove DMF. The ethers - were isolated after solvent evaporation without requiring further purification. (Prop--yn--yloxy)benzene () Η ΝΜR:. (dt, J =.0 Hz, J =.0 Hz, H),.0 (t, J=.0 Hz, H),. (d, J=. Hz, H),.0 (t, J=. Hz, H). C NMR:.,.,.,.,.,.,.. -thyl--(prop--yn--yloxy)benzene () Η ΝΜR:.0 (d, J=. Hz, H),. (d, J=. Hz, H),. (d, J=. Hz, H),.0 (t, J=. Hz, H),. (s, H). C NMR:., 0.,.,.,.,.,., 0..
3 -thoxy--(prop--yn--yloxy)benzene () Η ΝΜR:. (d, J=.0 Hz, H),. (d, J=.0 Hz, H),. (d, J=. Hz, H),. (s, H),. (t, J=. Hz, H). C NMR:.,.,.,.,.,.,.,.. -Fluoro--(prop--yn--yloxy)benzene () Η ΝΜR:. (m, H),. (d, J=. Hz, H),. (t, J=. Hz, H). C NMR:. (d, J=.0 Hz),. (d, J=.0 Hz),. (d, J=.0 Hz),. (d, J=.0 Hz),.,.,.. -Bromo--(prop--yn--yloxy)benzene () Η ΝΜR:. (d, J=.0 Hz, H),. (d, J=.0 Hz, H),. (d, J=. Hz, H),. (t, J=. Hz, H). C NMR:.,.,.,.,.,.,.0. -(Prop--yn--yloxy)naphthalene () Η ΝΜR:. (m, H),. (m, H),.-. (m, H),.0 (t, J=.0 Hz, H),. (d, J=. Hz, H),. (q, J=. Hz, H). C NMR:.,.,.,.,.,.,.,.0,., 0.,.,.,.. -(But--yn--yloxy)--methoxybenzene () Η ΝΜR:. (d, J=. Hz, H),. (d, J =. Hz, H),. (q, J=. Hz, H),. (s, H),. (t, J=. Hz, H).
4 C NMR:.,.,.,.,.,.,.,.,.. (But--yn--yloxy)benzene () Η ΝΜR:.0 (m, H),. (t, J=.0 Hz, H),. (d, J=.0 Hz, H),. (t, J=.0 Hz, H). C NMR:.,.,.,.,.,.0,.,.. -(But--yn--yloxy)naphthalene () Η ΝΜR:. (m, H),. (m, H),.-.0 (m, H),. (d, J=. Hz, H),. (d, J=.0 Hz, H),. (d, J=.0 Hz, H). C NMR:.,.,.,.,.,.,.,., 0., 0.,.,.,.,.. Synthesis of aryl propargyl ethers 0- In flame dried flask were placed mmol of phenol and ml of anhydrous CH CN. At 0 ο C were subsequently added. mmol of DBU, a catalytic amount (%) of CuCl H and 0. mmol of -chloro--methyl--butyne. The reaction progress was monitored by TLC and was completed after approximately 0 h at room temperature. Diethyl ether was added and the organic layer was washed with dilute HCl and brine. The ethers 0- were isolated in pure form after chromatographic purification (isolated yields: % for 0, % for, and % for ). ((-thylbut--yn--yl)oxy)benzene (0)
5 Η ΝΜR:. (m, H),.0 (m, H),. (s, H),. (s, H). C NMR:.,.,.,.,.,.,.,.. -thoxy--((-methylbut--yn--yl)oxy)benzene () Η ΝΜR:. (d, J=.0 Hz, H),. (d, J=.0 Hz, H),. (s, H),. (s, H),.0 (s, H). C NMR:.,.,.,.,.,.,.,.,.0,.,.. -((-thylbut--yn--yl)oxy)-h-chromen--one () Η ΝΜR:. (d, J=.0 Hz, H),. (d, J=. Hz, H),. (d, J=.0 Hz, H),.0 (dd, J =. Hz, J =.0 Hz, H),. (d, J=.0 Hz, H),. (s, H).. (s, H). C NMR:.,.,.0,.,.,.0,.,., 0.0,.,.,.,.. Characterization of the Au/Ti -catalyzed cyclization products H-Chromene (a) Η ΝΜR:. (t, J=. Hz, H),. (d, J=. Hz, H),. (t, J=. Hz, H),. (d, J=.0 Hz, H),. (d, J=. Hz, H),. (dt, J =. Hz, J =. Hz, H),. (m, H). C NMR:.0,.,.,.,.,.,.,.,.. H,'H-,'-Bichromene (b) Η ΝΜR:. (dt, J =.0 Hz, J =. Hz, H),.0 (dd, J =.0 Hz, J =. Hz, H),.0 (dt, J =.0 Hz, J =0. Hz, H),. (d, J=.0 Hz, H),. (s, H),.0 (s, H). C NMR:.,.,.,.,.,.,.,.,..
6 MS (EI): (M +, 00%), (%), (%), (%), (%), 0 (%), (%), (0%). -thyl-h-chromene (a) Η ΝΜR:.0 (dd, J =.0 Hz, J =.0 Hz, H),. (s, H),. (d, J=.0 Hz, H),. (br d, J=. Hz, H),. (dt, J =. Hz, J =. Hz, H),. (m, H),. (s, H). C NMR:., 0.,.,.,.,.,.0,.,., 0..,'-Dimethyl-H,'H-,'-bichromene (b) Η ΝΜR:. (d, J=.0 Hz, H),. (s, H),. (d, J=.0 Hz, H),. (s, H),.0 (s, H),. (s, H). C NMR:., 0.,.,.,.,.,.,.,., 0.. MS (EI): 0 (M +, %), (00%), (0%), (%), 0 (%), (0%), (%). HRMS: calcd for C 0 H +H,.; found.. -thoxy-h-chromene (a) Η ΝΜR:. (d, J=. Hz, H),. (dd, J =. Hz, J =.0 Hz, H),. (d, J=.0 Hz, H),. (d, J=. Hz, H),. (td, J =. Hz, J =. Hz, H),. (m, H),. (s, H). C NMR:.,.,.,.,.0,.,.,.,.,..,'-Dimethoxy-H,'H-,'-bichromene (b) Η ΝΜR:. (d, J=.0 Hz, H),. (dd, J =.0 Hz, J =. Hz, H),. (d, J=. Hz, H),. (s, H),.0 (s, H),. (s, H). C NMR:.,.,.,.0,.,.,.,.,.,..
7 MS (EI): (M +, 00%), 0 (%), (%), (0%), (%). HRMS: calcd for C 0 H +Na,.0; found.0. -Fluoro-H-chromene (a) 0 Η ΝΜR:.-.0 (m, H),. (td, J =0.0 Hz, J =. Hz, H),. (td, J =. Hz, J =. Hz, H),. (m, H). C NMR:. (d, J=.0 Hz),. (d, J=. Hz),.0 (d, J=.0 Hz),. (d, J=.0 Hz),.,.,.0 (d, J=.0 Hz),. (d, J=. Hz),..,'-Difluoro-H,'H-,'-bichromene (b) Η ΝΜR:.-. (m, H),. (s, H),.0 (s, H). C NMR:. (d, J=. Hz),.,.,.,.,. (d, J=.0 Hz),. (d, J=.0 Hz),. (d, J=.0 Hz),.. MS (EI): (M +, %), (00%), (%), (%), 0 (%), (%), (%), (%), 0 (%), (%). HRMS: calcd for C H F,.00; found.00. -Bromo-H-chromene (a) Η ΝΜR:. (dd, J =. Hz, J =.0 Hz, H).0 (d, J=.0 Hz, H),. (d, J=. Hz, H),. (br d, J=. Hz, H),.0 (td, J =. Hz, J =. Hz, H),. (m, H). C NMR:.,.,.0,.,.,.,.,.,..,'-Dibromo-H,'H-,'-bichromene (b) Η ΝΜR:. (dd, J =. Hz, J =.0 Hz, H),. (d, J=.0 Hz, H),. (d, J=. Hz, H),. (s, H),.0 (s, H). C NMR:.,.,.,.,.,.0,.,.,..
8 MS (EI): 0 (M +, %), 0 (%), (%), 0 (%), 0 (00%). HRMS: calcd for C H Br,.0; found.0. H-Benzo[h]chromene (a) Η ΝΜR:. (m, H),. (m, H),. (m, H),. (d, J=. Hz, H),. (dd, J =. Hz, J =. Hz, H),. (td, J =. Hz, J =. Hz, H),.0 (m, H). C NMR:.,.,.,.,.,.,.,.,., 0., 0.,.,.. H,'H-,'-Dibenzo[h]chromene (b) This compound was formed in ~% relative yield and could be isolated. Η ΝΜR (characteristic absorptions from the crude reaction mixture):. (s, H),. (s, H). MS (EI): (M +, %), (%), (%), 0 (%), (00%), (0%), (%), (%). -thoxy--methyl-h-chromene (a) Η ΝΜR:.-. (m, H),. (m, H),. (m, H),. (s, H),.00 (q, J=.0 Hz, H). C NMR:.0,.0, 0.,.,.,.0,., 0.,.,.,.. -thyl-h-chromene (a) Η ΝΜR:. (m, H),. (dt, J =. Hz, J =.0 Hz, H),.0 (d, J=. Hz, H),. (br s, H),. (m, H),.0 (q, J=. Hz, H). C NMR:., 0.,.,.,.,.,.,.,.,..
9 -thyl-h-benzo[h]chromene (a) Η ΝΜR:.0 (m, H),. (m, H),.-. (m, H),. (br s, H),. (br s, H),. (s, H). C NMR:.,.,.,.,.,.,.,.,., 0.,.,.,.,..,-Dimethyl-H-chromene (0a) Η ΝΜR:.0 (dt, J =.0 Hz, J =.0 Hz, H),. (dd, J =.0 Hz, J =. Hz, H),. (dt, J =. Hz, J =.0 Hz, H),. (d, J=.0 Hz, H),. (d, J=0.0 Hz, H),. (d, J=0.0 Hz, H),. (s, H). C NMR:., 0.,.0,.,.,., 0.,.,.,.0.,,','-Tetramethyl-H,'H-,'-bichromene (0b) Η ΝΜR:. (dt, J =. Hz, J =. Hz, H),.0 (dd, J =. Hz, J =. Hz, H),.-. (m, H),.0 (s, H),. (s, H). C NMR:.,.,.,.,.,.,.,.,.,.. MS (EI): (M +, %), 0 (00%), (%), (%), (%), 0 (%). HRMS: calcd for C H +H,.; found.. -thoxy-,-dimethyl-h-chromene (a) Η ΝΜR:. (d, J=. Hz, H),. (br d, J=. Hz, H),. (br s, H),. (d, J=. Hz, H),. (d, J=. Hz, H),. (s, H),. (s, H). C NMR:.,.,.,.,.,.,.,.,.,.,..,'-Dimethoxy-,,','-tetramethyl-H,'H-,'-bichromene (b)
10 0 Η ΝΜR:. (d, J=. Hz, H),. (br d, J=. Hz, H),.0 (br s, H),. (s, H),. (s, H),. (s, H). C NMR:.0,.,.,.0,.,.0,.,.,.,.,.. MS (EI): (M +, %), (00%), (%), (%), (%), (%). HRMS: calcd for C H +H,.0; found.0.,-dimethylpyrano[,-f]chromen-(h)-one (seselin, a) seselin (a) Η ΝΜR:. (d, J=. Hz, H),. (d, J=. Hz, H),. (d, J=0.0 Hz, H),. (d, J=. Hz, H),. (d, J=. Hz, H),. (d, J=0.0 Hz, H),. (s, H). C NMR:.,., 0.0,., 0.,.,.,.,.,., 0.,.,..,-Dimethylpyrano[,-g]chromen-(H)-one (xanthyletin, b) xanthyletin (b) Η ΝΜR:. (d, J=. Hz, H),.0 (s, H),. (s, H),. (d, J=0.0 Hz, H),. (d, J=. Hz, H),. (d, J=0.0 Hz, H),. (s, H). C NMR:.,.,.,.,.,., 0.,.,.0,., 0.,.,..,,','-Tetramethyl-[,'-bipyrano[,-g]chromene]-,'(H,'H)-dione (c) Η ΝΜR:. (d, J=. Hz, H),. (s, H),. (s, H),. (s, H),. (d, J=. Hz, H),. (s, H). c
11 C NMR: 0.,.0,.,.,.,.,.,.,.,., 0., 0.,.. HRMS: calcd for C H +H,.; found.. References. non, R. S.; Findlay, A. D.; Bissember, A. C.; Banwell, M. G. J. rg. Chem. 00,, Chaudhary, P. M.; Chavan, S. R. Shirazi, F.; Razdan, M.; Nimkar, P.; Maybhate, S. P.; Likhite, A. P.; Gonnade, R.; Hazara, B. G.; Deshpande, M. V.; Deshpande, S. R. Bioorg. d. Chem. 00,, -0.. Punna, S.; unier, S.; Finn, M. G. rg. Lett. 00,, -.. Worlikar, S. A.; Kesharwani, T.; Yao, T.; Larock, R. C. J. rg. Chem. 00,, -.. Savitha, G.; Felix, K.; Perumal, P. T. Synlett 00, Godfrey, J. D.; Mueller, R. H.; Sedergran, T. C.; Soundararajan, N.; Colandrea, V. J. Tetrahedron Lett.,, Wegner, H. A.; Ahles, S.; Neuburger, M. Chem. Eur. J. 00,, 0-.. Bell, D.; Davies, M. R.; Geen, G. R.; Mann, I. S. Synthesis, 0-.. Pillai, S. P.; non, S. R.; Mitscher, L. A.; Pillai, C. A.; Shankel, D. M. J. Nat. Prod.,, Antonov, D.; Sund, C.; Lindstroem, S.; Sahlberg, C. PCT Int. Appl. (00), W 000 A Furstner, A.; Guth,.; Duffels, A.; Seidel, G.; Liebl, M.; Gabor, B. Mynott, R. Chem. Eur. J. 00,, -0.. Chang S.; Grubbs, R. H. J. rg. Chem.,, -.. Balasubramanian, T.; Balasubramanian, K. K. J. Chem. Soc., Chem. Commun., 0-.. Pastine, S. J.; Youn, S. W.; Sames, D. Tetrahedron 00,, -.. Yamazaki S. rg. Biomol. Chem. 00,, -.. Aniol, M.; Wawrzenczyk, C. Heterocycles,, -.. Nicolaou, K. C.; Pfefferkorn, J. A.; Cao, G.-Q. Angew. Chem. Int. Ed. 000,, -.
12 H, C-NMR and MS/HRMS spectra of key compounds and reactions
13 H C 0 H C
14 H C 0 H C
15 F 0 F
16 Br 0 Br
17
18 H C CH 0 H C CH
19 CH 0 CH
20 0 CH 0 CH
21
22
23 * * 0 * = Diethyl ether
24 a * * 0 * = Diethyl ether a
25 Petroleum ether b 0 b % b Chemical Formula: C H Molecular Weight:,
26 H C a 0 H C a
27 Au/Ti H C a DCE, 0 o C h, crude spectrum H C ~0-% conversion * * * DCE * 0
28 H C CH H b 0 H C CH b
29 b H C CH % Chemical Formula: C 0 H Molecular Weight: 0, HRMS XPR000_SM00_0 # RT: 0.0 AV: NL:.E T: FTMS + p ESI Full ms [ ] MH +. H C b CH + H Chemical Formula: C 0 H + H 0 Relative Abundance m/z
30 0 H C a H 0 H C a
31 b H 0 b
32 b % Chemical Formula: C 0 H Molecular Weight:, HRMS
33 F a H 0 F a
34 F F b Acetone H 0 F F b
35 F b F % Chemical Formula: C H F Molecular Weight:, HRMS
36 Br a * * 0 * = Diethyl ether Br a
37 H Br Br b 0 Br Br b
38 b Br Br Chemical Formula: C H Br Molecular Weight: 0,0.0 % HRMS
39 a 0 a
40 0 Au/Ti crude mixture a + b a (H) b (H) Identification of dimer b by analysis of the crude reaction mixture by GC-MS b 00 % Chemical Formula: C H Molecular Weight:,
41 a 0 H C a
42 a H 0 a
43 a 0 a
44 0a 0 0a
45 0b H b
46 0b % Chemical Formula: C H Molecular Weight:, HRMS XPR000_SM00_0 #- RT: AV: NL:.E T: FTMS + p ESI Full ms [ ] MH + 0b 0 0 Chemical Formula: C H + H + H Relative Abundance m/z.0
47 a 0 a
48 b H 0 b
49 b Chemical Formula: C H Molecular Weight:, % HRMS xpr000_sm00_0 #- RT: AV: NL:.E T: FTMS + p ESI Full ms [ ] MH + b + H 0 Chemical Formula: C H + H 0 Relative Abundance m/z
50 0 a (seselin) * * 0 * = Diethyl ether a (seselin)
51 b (xanthyletin) 0 0 b (xanthyletin)
52 c (xanthyletin dimer) H 0 c (xanthyletin dimer)
53 HRMS xpr000_sm00_0 #0 RT:. AV: NL:.E T: FTMS + c ESI Full ms [ ] 00.0 MH + 0 Relative Abundance c (xanthyletin dimer) Chemical Formula: C H + H. + H m/z
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