selective reduction of condensed n-heterocycles using water ...selective reduction of condensed...

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Selective reduction of condensed N-heterocycles using water as solvent and hydrogen source Hyejin Cho, Fanni Török and Béla Török* * To whom correspondence should be addressed Béla Török, email: [email protected], Phone: 617-287-6159 Department of Chemistry, University of Massachusetts Boston, 100 Morrissey Blvd. Boston, MA 02125, USA. Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is © The Royal Society of Chemistry 2012

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Page 1: Selective reduction of condensed N-heterocycles using water ...Selective reduction of condensed N-heterocycles using water as solvent and hydrogen source Hyejin Cho, Fanni Török

Selective reduction of condensed N-heterocycles using water as

solvent and hydrogen source

Hyejin Cho, Fanni Török and Béla Török*

* To whom correspondence should be addressed

Béla Török, email: [email protected], Phone: 617-287-6159

Department of Chemistry, University of Massachusetts Boston, 100 Morrissey Blvd. Boston,

MA 02125, USA.

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

Page 2: Selective reduction of condensed N-heterocycles using water ...Selective reduction of condensed N-heterocycles using water as solvent and hydrogen source Hyejin Cho, Fanni Török

1H NMR of 1

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

Page 3: Selective reduction of condensed N-heterocycles using water ...Selective reduction of condensed N-heterocycles using water as solvent and hydrogen source Hyejin Cho, Fanni Török

13C NMR of 1

 

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

Page 4: Selective reduction of condensed N-heterocycles using water ...Selective reduction of condensed N-heterocycles using water as solvent and hydrogen source Hyejin Cho, Fanni Török

1H NMR of 2

 

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

Page 5: Selective reduction of condensed N-heterocycles using water ...Selective reduction of condensed N-heterocycles using water as solvent and hydrogen source Hyejin Cho, Fanni Török

13C NMR of 2

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

Page 6: Selective reduction of condensed N-heterocycles using water ...Selective reduction of condensed N-heterocycles using water as solvent and hydrogen source Hyejin Cho, Fanni Török

1H NMR of 3

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

Page 7: Selective reduction of condensed N-heterocycles using water ...Selective reduction of condensed N-heterocycles using water as solvent and hydrogen source Hyejin Cho, Fanni Török

13C NMR of 3

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

Page 8: Selective reduction of condensed N-heterocycles using water ...Selective reduction of condensed N-heterocycles using water as solvent and hydrogen source Hyejin Cho, Fanni Török

1H NMR of 4

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

Page 9: Selective reduction of condensed N-heterocycles using water ...Selective reduction of condensed N-heterocycles using water as solvent and hydrogen source Hyejin Cho, Fanni Török

13C NMR of 4

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

Page 10: Selective reduction of condensed N-heterocycles using water ...Selective reduction of condensed N-heterocycles using water as solvent and hydrogen source Hyejin Cho, Fanni Török

1H NMR of 5

 

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

Page 11: Selective reduction of condensed N-heterocycles using water ...Selective reduction of condensed N-heterocycles using water as solvent and hydrogen source Hyejin Cho, Fanni Török

13C NMR of 5

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

Page 12: Selective reduction of condensed N-heterocycles using water ...Selective reduction of condensed N-heterocycles using water as solvent and hydrogen source Hyejin Cho, Fanni Török

1H NMR of 6

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

Page 13: Selective reduction of condensed N-heterocycles using water ...Selective reduction of condensed N-heterocycles using water as solvent and hydrogen source Hyejin Cho, Fanni Török

13C NMR of 6

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

Page 14: Selective reduction of condensed N-heterocycles using water ...Selective reduction of condensed N-heterocycles using water as solvent and hydrogen source Hyejin Cho, Fanni Török

1H NMR of 7

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

Page 15: Selective reduction of condensed N-heterocycles using water ...Selective reduction of condensed N-heterocycles using water as solvent and hydrogen source Hyejin Cho, Fanni Török

13C NMR of 7

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

Page 16: Selective reduction of condensed N-heterocycles using water ...Selective reduction of condensed N-heterocycles using water as solvent and hydrogen source Hyejin Cho, Fanni Török

1H NMR of 8

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

Page 17: Selective reduction of condensed N-heterocycles using water ...Selective reduction of condensed N-heterocycles using water as solvent and hydrogen source Hyejin Cho, Fanni Török

13C NMR of 8

 

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

Page 18: Selective reduction of condensed N-heterocycles using water ...Selective reduction of condensed N-heterocycles using water as solvent and hydrogen source Hyejin Cho, Fanni Török

1H NMR of 9

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

Page 19: Selective reduction of condensed N-heterocycles using water ...Selective reduction of condensed N-heterocycles using water as solvent and hydrogen source Hyejin Cho, Fanni Török

13C NMR of 9

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

Page 20: Selective reduction of condensed N-heterocycles using water ...Selective reduction of condensed N-heterocycles using water as solvent and hydrogen source Hyejin Cho, Fanni Török

1H NMR of 10

 

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

Page 21: Selective reduction of condensed N-heterocycles using water ...Selective reduction of condensed N-heterocycles using water as solvent and hydrogen source Hyejin Cho, Fanni Török

13C NMR of 10

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

Page 22: Selective reduction of condensed N-heterocycles using water ...Selective reduction of condensed N-heterocycles using water as solvent and hydrogen source Hyejin Cho, Fanni Török

1H NMR of 11

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

Page 23: Selective reduction of condensed N-heterocycles using water ...Selective reduction of condensed N-heterocycles using water as solvent and hydrogen source Hyejin Cho, Fanni Török

13C NMR of 11

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

Page 24: Selective reduction of condensed N-heterocycles using water ...Selective reduction of condensed N-heterocycles using water as solvent and hydrogen source Hyejin Cho, Fanni Török

1H NMR of 12

 

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

Page 25: Selective reduction of condensed N-heterocycles using water ...Selective reduction of condensed N-heterocycles using water as solvent and hydrogen source Hyejin Cho, Fanni Török

13C NMR of 12

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

Page 26: Selective reduction of condensed N-heterocycles using water ...Selective reduction of condensed N-heterocycles using water as solvent and hydrogen source Hyejin Cho, Fanni Török

1H NMR of 13

 

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

Page 27: Selective reduction of condensed N-heterocycles using water ...Selective reduction of condensed N-heterocycles using water as solvent and hydrogen source Hyejin Cho, Fanni Török

13C NMR of 13

 

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

Page 28: Selective reduction of condensed N-heterocycles using water ...Selective reduction of condensed N-heterocycles using water as solvent and hydrogen source Hyejin Cho, Fanni Török

1H NMR of 14

 

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

Page 29: Selective reduction of condensed N-heterocycles using water ...Selective reduction of condensed N-heterocycles using water as solvent and hydrogen source Hyejin Cho, Fanni Török

13C NMR of 14

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

Page 30: Selective reduction of condensed N-heterocycles using water ...Selective reduction of condensed N-heterocycles using water as solvent and hydrogen source Hyejin Cho, Fanni Török

1H NMR of 15

 

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

Page 31: Selective reduction of condensed N-heterocycles using water ...Selective reduction of condensed N-heterocycles using water as solvent and hydrogen source Hyejin Cho, Fanni Török

13C NMR of 15

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

Page 32: Selective reduction of condensed N-heterocycles using water ...Selective reduction of condensed N-heterocycles using water as solvent and hydrogen source Hyejin Cho, Fanni Török

1H NMR of 16

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

Page 33: Selective reduction of condensed N-heterocycles using water ...Selective reduction of condensed N-heterocycles using water as solvent and hydrogen source Hyejin Cho, Fanni Török

13C NMR of 16

 

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012