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S1 / S27 Supporting information Copper-mediated thiolation of carbazole derivatives and related N- heterocycle compounds Longzhi Zhu, a Xin Cao, a Renhua Qiu, a,b* Takanori Iwasaki, b Vutukuri Prakash Reddy, b Xinhua Xu, a Shuang-Feng Yin a* and Nobuaki Kambe a,b* a College of Chemistry and Chemical Engineering, Hunan University, Changsha, 410082, P.R. China; b Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka, 565-0871, Japan ; [email protected]; [email protected]; [email protected] Electronic Supplementary Material (ESI) for RSC Advances. This journal is © The Royal Society of Chemistry 2015

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Page 1: heterocycle compounds Copper-mediated thiolation of ...S1 / S27 Supporting information Copper-mediated thiolation of carbazole derivatives and related N- heterocycle compounds Longzhi

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Supporting information

Copper-mediated thiolation of carbazole derivatives and related N-heterocycle compounds

Longzhi Zhu,a Xin Cao,a Renhua Qiu,a,b*Takanori Iwasaki,b Vutukuri Prakash Reddy,b Xinhua Xu,a

Shuang-Feng Yina* and Nobuaki Kambea,b*

aCollege of Chemistry and Chemical Engineering, Hunan University, Changsha, 410082, P.R. China;

bDepartment of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka, 565-0871, Japan ;

[email protected]; [email protected]; [email protected]

Electronic Supplementary Material (ESI) for RSC Advances.This journal is © The Royal Society of Chemistry 2015

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1. Data of 1H NMR and 13C NMR of Compounds of 3a-3l, 5a-5e, 7a-7g, 9 and 1b.

1-(Phenylthio)-9-(pyrimidin-2-yl)-9H-carbazole (3a)

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1-((4-Methylphenyl)thio)-9-(pyrimidin-2-yl)-9H-carbazole(3b)

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1-(4-Chlorophenyl)thio)-9-(pyrimidin-2-yl)-9H-carbazole (3c)

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1-((4-Bromophenyl)thio)-9-(pyrimidin-2-yl)-9H-carbazole (3d)

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1-((4-Methoxyphenyl)thio)-9-(pyrimidin-2-yl)-9H-carbazole (3e)

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1-((2-Nitrophenyl)thio)-9-(pyrimidin-2-yl)-9H-carbazole (3f)

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1-((3-Nitrophenyl)thio)-9-(pyrimidin-2-yl)-9H-carbazole (3g)

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1-((4-Nitrophenyl)thio)-9-(pyrimidin-2-yl)-9H-carbazole (3h)

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1-(Cyclohexylthio)-9-(pyrimidin-2-yl)-9H-carbazole (3i)

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1-(Propylthio)-9-(pyrimidin-2-yl)-9H-carbazole (3j)

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1-(Benzylthio)-9-(pyrimidin-2-yl)-9H-carbazole (3k)

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Methyl 3-((9-(pyrimidin-2-yl)-9H-carbazol-1-yl)thio)propano-ate(3l)

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10-(Phenylthio)benzo[h]quinoline (5a)

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10-((4-Methylphenyl)thio)benzo[h]quinoline (5b)

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10-((4-chlorophenyl)thio)benzo[h]quinoline (5c)

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10-((4-methoxyphenyl)thio)benzo[h]quinoline (5d)

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10-(Propylthio)benzo[h]quinoline (5e)

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2-((Phenylthio)thio)-1-(pyrimidin-2-yl)-1H-indole (7a)

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2-((4-methlphenyl)thio)-1-(pyrimidin-2-yl)-1H-indole (7b)

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2-((4-Methoxyphenyl)thio)-1-(pyrimidin-2-yl)-1H-indole (7c)

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2-((4-Chlorophenyl)thio)-1-(pyrimidin-2-yl)-1H-indole (7d)

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2-((4-Nitroxyphenyl)thio)-1-(pyrimidin-2-yl)-1H-indole (7e)

2-((Benzyl)thio)-1-(pyrimidin-2-yl)-1H-indole (7f)

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2-( Cyclohexylthio)-1-(pyrimidin-2-yl)-1H-indole (7g)

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2-(2-(phenylthio)phenyl)quinolone(9)

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N-Phenyl carbazole (1b)