Supporting Information

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Hana Štěpánková
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1 Supporting Information Catalytic Activation of Trimethylsilylacetylenes: A One Pot Route to Unsymmetrical Acetylenes and Heterocycles Dániel Lasányi, Ádám Mészáros, Zoltán Novák, * Gergely L. Tolnai* Institute of Chemistry, Eötvös University, Pázmány P. stny 1/a, H1117, Budapest, Hungary novakz@elte.hu; web: tolnai@chem.elte.hu, web: SI-1

2 Contents Supporting Information... SI-1 Contents... SI-2 Spectra of Starting Materials... SI-4 Triethyl((3-iodobenzyl)oxy)silane 1w... SI-4 tert-butyl((3-iodobenzyl)oxy)diphenylsilane 1x:... SI-5 tert-butyl((3-iodobenzyl)oxy)dimethylsilane 1y... SI-6 ((3-Iodobenzyl)oxy)triisopropylsilane 1z:... SI-7 5-Iodo-3-((triisopropylsilyl)ethynyl)-1H-indole. 1aa:... SI-8 Spectra of Unsymmetric Acetylenes... SI-9 Scope(I)... SI-9 1,2-Diphenylethyne 3a... SI-9 1-(4-(Phenylethynyl)phenyl)ethan-1-one 3b... SI-10 1-Methoxy-4-(phenylethynyl)benzene 3c... SI-11 1-Methyl-4-(phenylethynyl)benzene 3d... SI-12 3-(Phenylethynyl)aniline 3e... SI-13 3-(Phenylethynyl)benzonitrile 3f... SI-14 3-(Phenylethynyl)pyridine 3g... SI-15 2-(Phenylethynyl)thiophene 3h... SI-16 5-(Phenylethynyl)-1H-indole 3i... SI-17 6-(Phenylethynyl)quinoline 3j... SI-18 Scope(II)... SI-19 Methyl 4-(thiophen-2-ylethynyl)benzoate 3k... SI-19 5-(Thiophen-2-ylethynyl)-1H-indole 3l... SI-20 2-((3,5-bis(Trifluoromethyl)phenyl)ethynyl)thiophene 3m... SI-21 1-((3-Fluorophenyl)ethynyl)-3,5-dimethylbenzene 3n... SI-23 1-Chloro-4-((4-fluorophenyl)ethynyl)benzene 3o... SI-25 1-Methoxy-4-((4-nitrophenyl)ethynyl)benzene 3p... SI-27 5-Chloro-2-(p-tolylethynyl)aniline 3q... SI-28 2-((4-Chlorophenyl)ethynyl)-4-(trifluoromethyl)aniline 3r... SI-29 3-((3-Bromophenyl)ethynyl)-2-methylquinolin-4- amine 3s... SI-31 7-Chloro-4-(phenylethynyl)quinolone 3t... SI-32 1,4-bis(Phenylethynyl)benzene 3u... SI-33 2-(Naphthalen-2-ylethynyl)-9H-fluorene 3v... SI-34 Selective Catalityc Activation of Trimethylsilylacetylene... SI-35 SI-2

3 Triethyl((3-(phenylethynyl)benzyl)oxy)silane 3w... SI-35 tert-butyldiphenyl((3-(phenylethynyl)benzyl)oxy)silane 3x... SI-36 tert-butyldimethyl((3-(phenylethynyl)benzyl)oxy)silane 3y... SI-37 Triisopropyl((3-(phenylethynyl)benzyl)oxy)silane 3z... SI-38 5-(Pyridin-2-ylethynyl)-3-((triisopropylsilyl)ethynyl)-1H-indole 3aa... SI-39 Spectra of Benzofuranes with One-Pot Catalytic Deprotection... SI-40 Ethyl 4-(benzofuran-2-yl)benzoate 4a... SI-40 2-(4-Methoxyphenyl)benzofuran 4b... SI-41 2-(4-Nitrophenyl)benzofuran 4c... SI-42 Methyl 2-(1H-indol-5-yl)benzofuran-6-carboxylate 4d... SI-43 6-Chloro-2-(thiophen-2-yl)benzofuran 4e... SI-44 7-Chloro-4-(5-fluorobenzofuran-2-yl)quinoline 4f... SI-45 Spectra of Triazoles with One-Pot Catalytic Deprotection... SI-47 5-(1-(4-Bromobenzyl)-1H-1,2,3-triazol-4-yl)-1H-indole 5a... SI-47 4-(3-Bromophenyl)-1-(4-nitrobenzyl)-1H-1,2,3-triazole 5b... SI-48 4-(1-(4-Bromobenzyl)-1H-1,2,3-triazol-4-yl)-7-chloroquinoline 5c... SI-49 SI-3

4 Spectra of Starting Materials Triethyl((3-iodobenzyl)oxy)silane 1w Spectra SI-4

5 tert-butyl((3-iodobenzyl)oxy)diphenylsilane 1x: SI-5

6 tert-butyl((3-iodobenzyl)oxy)dimethylsilane 1y SI-6

7 ((3-Iodobenzyl)oxy)triisopropylsilane 1z: SI-7

8 5-Iodo-3-((triisopropylsilyl)ethynyl)-1H-indole. 1aa: SI-8

9 Spectra of Unsymmetric Acetylenes Scope(I) 1,2-Diphenylethyne 3a SI-9

10 1-(4-(Phenylethynyl)phenyl)ethan-1-one 3b SI-10

11 1-Methoxy-4-(phenylethynyl)benzene 3c SI-11

12 1-Methyl-4-(phenylethynyl)benzene 3d SI-12

13 3-(Phenylethynyl)aniline 3e SI-13

14 3-(Phenylethynyl)benzonitrile 3f SI-14

15 3-(Phenylethynyl)pyridine 3g SI-15

16 2-(Phenylethynyl)thiophene 3h SI-16

17 5-(Phenylethynyl)-1H-indole 3i SI-17

18 6-(Phenylethynyl)quinoline 3j SI-18

19 Scope(II) Methyl 4-(thiophen-2-ylethynyl)benzoate 3k SI-19

20 5-(Thiophen-2-ylethynyl)-1H-indole 3l SI-20

21 2-((3,5-bis(Trifluoromethyl)phenyl)ethynyl)thiophene 3m SI-21

22 SI-22

23 1-((3-Fluorophenyl)ethynyl)-3,5-dimethylbenzene 3n SI-23

24 SI-24

25 1-Chloro-4-((4-fluorophenyl)ethynyl)benzene 3o SI-25

26 SI-26

27 1-Methoxy-4-((4-nitrophenyl)ethynyl)benzene 3p SI-27

28 5-Chloro-2-(p-tolylethynyl)aniline 3q SI-28

29 2-((4-Chlorophenyl)ethynyl)-4-(trifluoromethyl)aniline 3r SI-29

30 SI-30

31 3-((3-Bromophenyl)ethynyl)-2-methylquinolin-4- amine 3s SI-31

32 7-Chloro-4-(phenylethynyl)quinolone 3t SI-32

33 1,4-bis(Phenylethynyl)benzene 3u SI-33

34 2-(Naphthalen-2-ylethynyl)-9H-fluorene 3v SI-34

35 Selective Catalityc Activation of Trimethylsilylacetylene Triethyl((3-(phenylethynyl)benzyl)oxy)silane 3w SI-35

36 tert-butyldiphenyl((3-(phenylethynyl)benzyl)oxy)silane 3x SI-36

37 tert-butyldimethyl((3-(phenylethynyl)benzyl)oxy)silane 3y SI-37

38 Triisopropyl((3-(phenylethynyl)benzyl)oxy)silane 3z SI-38

39 5-(Pyridin-2-ylethynyl)-3-((triisopropylsilyl)ethynyl)-1H-indole 3aa SI-39

40 Spectra of Benzofuranes with One-Pot Catalytic Deprotection Ethyl 4-(benzofuran-2-yl)benzoate 4a SI-40

41 2-(4-Methoxyphenyl)benzofuran 4b SI-41

42 2-(4-Nitrophenyl)benzofuran 4c SI-42

43 Methyl 2-(1H-indol-5-yl)benzofuran-6-carboxylate 4d SI-43

44 6-Chloro-2-(thiophen-2-yl)benzofuran 4e SI-44

45 7-Chloro-4-(5-fluorobenzofuran-2-yl)quinoline 4f SI-45

46 SI-46

47 Spectra of Triazoles with One-Pot Catalytic Deprotection 5-(1-(4-Bromobenzyl)-1H-1,2,3-triazol-4-yl)-1H-indole 5a SI-47

48 4-(3-Bromophenyl)-1-(4-nitrobenzyl)-1H-1,2,3-triazole 5b SI-48

49 4-(1-(4-Bromobenzyl)-1H-1,2,3-triazol-4-yl)-7-chloroquinoline 5c SI-49

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