csf/clinoptilolite: an efficient solid base in snar · 2015-12-16 · 1" "...

20
1 CsF/Clinoptilolite: an Efficient Solid Base in S N Ar and Copper-catalyzed Ullmann Reactions Hoda Keipour a,b , Abolfazl Hosseini b , Amir Afsari b , Razieh Oladee b , Mohammad A. Khalilzadeh* b and Thierry Ollevier* a a Département de chimie, Université Laval, 1045 avenue de la Médecine, Québec, QC, G1V 0A6, Canada Fax: +14186567916; E-mail: [email protected] b Department of Chemistry, Qaemshahr Branch, Islamic Azad University, Qaemshahr, Iran Fax: +981232211647; E-mail: [email protected]

Upload: others

Post on 17-Jul-2020

3 views

Category:

Documents


0 download

TRANSCRIPT

Page 1: CsF/Clinoptilolite: an Efficient Solid Base in SNAr · 2015-12-16 · 1" " CsF/Clinoptilolite: an Efficient Solid Base in S NAr and Copper-catalyzed Ullmann Reactions " Hoda Keipoura,b,

1  

 

CsF/Clinoptilolite: an Efficient Solid Base in SNAr

and Copper-catalyzed Ullmann Reactions  

 

Hoda Keipoura,b, Abolfazl Hosseinib, Amir Afsarib, Razieh Oladeeb,

Mohammad A. Khalilzadeh*b and Thierry Ollevier*a

 

a Département de chimie, Université Laval, 1045 avenue de la Médecine, Québec, QC, G1V 0A6, Canada

Fax: +14186567916; E-mail: [email protected]

b Department of Chemistry, Qaemshahr Branch, Islamic Azad University, Qaemshahr, Iran

Fax: +981232211647; E-mail: [email protected]

 

 

Page 2: CsF/Clinoptilolite: an Efficient Solid Base in SNAr · 2015-12-16 · 1" " CsF/Clinoptilolite: an Efficient Solid Base in S NAr and Copper-catalyzed Ullmann Reactions " Hoda Keipoura,b,

2  

 

1H-NMR spectrum 1-fluoro-3-(4-nitrophenoxy)benzene (Table 2, entry 1)

1H-NMR spectrum 1-fluoro-3-(4-nitrophenoxy)benzene (Table 2, entry 1)

Page 3: CsF/Clinoptilolite: an Efficient Solid Base in SNAr · 2015-12-16 · 1" " CsF/Clinoptilolite: an Efficient Solid Base in S NAr and Copper-catalyzed Ullmann Reactions " Hoda Keipoura,b,

3  

 

1H-NMR spectrum 1-fluoro-3-(4-nitrophenoxy)benzene (Table 2, entry 1)

1H-NMR spectrum 1-fluoro-3-(4-nitrophenoxy)benzene (Table 2, entry 1)

Page 4: CsF/Clinoptilolite: an Efficient Solid Base in SNAr · 2015-12-16 · 1" " CsF/Clinoptilolite: an Efficient Solid Base in S NAr and Copper-catalyzed Ullmann Reactions " Hoda Keipoura,b,

4  

 

13C-NMR spectrum 1-fluoro-3-(4-nitrophenoxy)benzene (Table 2, entry 1)

13C-NMR spectrum 1-fluoro-3-(4-nitrophenoxy)benzene (Table 2, entry 1)

Page 5: CsF/Clinoptilolite: an Efficient Solid Base in SNAr · 2015-12-16 · 1" " CsF/Clinoptilolite: an Efficient Solid Base in S NAr and Copper-catalyzed Ullmann Reactions " Hoda Keipoura,b,

5  

 

1H-NMR spectrum 1-fluoro-4-(4-nitrophenoxy)benzene (Table 2, entry 2)

1H-NMR spectrum 1-fluoro-4-(4-nitrophenoxy)benzene (Table 2, entry 2)

Page 6: CsF/Clinoptilolite: an Efficient Solid Base in SNAr · 2015-12-16 · 1" " CsF/Clinoptilolite: an Efficient Solid Base in S NAr and Copper-catalyzed Ullmann Reactions " Hoda Keipoura,b,

6  

 

13C-NMR spectrum 1-fluoro-4-(4-nitrophenoxy)benzene (Table 2, entry 2)

13C-NMR spectrum 1-fluoro-4-(4-nitrophenoxy)benzene (Table 2, entry 2)

Page 7: CsF/Clinoptilolite: an Efficient Solid Base in SNAr · 2015-12-16 · 1" " CsF/Clinoptilolite: an Efficient Solid Base in S NAr and Copper-catalyzed Ullmann Reactions " Hoda Keipoura,b,

7  

 

1H-NMR spectrum 1-chloro-3-(4-nitrophenoxy)benzene (Table 2, entry 4)

1H-NMR spectrum 1-chloro-3-(4-nitrophenoxy)benzene (Table 2, entry 4)

Page 8: CsF/Clinoptilolite: an Efficient Solid Base in SNAr · 2015-12-16 · 1" " CsF/Clinoptilolite: an Efficient Solid Base in S NAr and Copper-catalyzed Ullmann Reactions " Hoda Keipoura,b,

8  

 

1H-NMR spectrum 1-chloro-3-(4-nitrophenoxy)benzene (Table 2, entry 4)

13C-NMR spectrum  1-chloro-3-(4-nitrophenoxy)benzene (Table 2, entry 4)

Page 9: CsF/Clinoptilolite: an Efficient Solid Base in SNAr · 2015-12-16 · 1" " CsF/Clinoptilolite: an Efficient Solid Base in S NAr and Copper-catalyzed Ullmann Reactions " Hoda Keipoura,b,

9  

 

1H-NMR spectrum 1-iodo-4-(4-nitrophenoxy)benzene (Table 2, entry 9)

1H-NMR spectrum 1-iodo-4-(4-nitrophenoxy)benzene (Table 2, entry 9)

Page 10: CsF/Clinoptilolite: an Efficient Solid Base in SNAr · 2015-12-16 · 1" " CsF/Clinoptilolite: an Efficient Solid Base in S NAr and Copper-catalyzed Ullmann Reactions " Hoda Keipoura,b,

10  

 

13C-NMR spectrum 1-iodo-4-(4-nitrophenoxy)benzene (Table 2,entry 9)

Page 11: CsF/Clinoptilolite: an Efficient Solid Base in SNAr · 2015-12-16 · 1" " CsF/Clinoptilolite: an Efficient Solid Base in S NAr and Copper-catalyzed Ullmann Reactions " Hoda Keipoura,b,

11  

 

1H-NMR spectrum 1,3-dimethyl-5-(4-nitrophenoxy)benzene (Table 2, entry 13)

1H-NMR spectrum 1,3-dimethyl-5-(4-nitrophenoxy)benzene (Table 2, entry 13)

Page 12: CsF/Clinoptilolite: an Efficient Solid Base in SNAr · 2015-12-16 · 1" " CsF/Clinoptilolite: an Efficient Solid Base in S NAr and Copper-catalyzed Ullmann Reactions " Hoda Keipoura,b,

12  

 

1H-NMR spectrum 1,3-dimethyl-5-(4-nitrophenoxy)benzene (Table 2, entry 13)

13C-NMR spectrum 1,3-dimethyl-5-(4-nitrophenoxy)benzene (Table 2, entry 13)

Page 13: CsF/Clinoptilolite: an Efficient Solid Base in SNAr · 2015-12-16 · 1" " CsF/Clinoptilolite: an Efficient Solid Base in S NAr and Copper-catalyzed Ullmann Reactions " Hoda Keipoura,b,

13  

 

13C-NMR spectrum 1,3-dimethyl-5-(4-nitrophenoxy)benzene (Table 2,entry 13)

1H-NMR spectrum 1,3-di-tert-butyl-2-(4-nitrophenoxy)benzene (Table 2,entry 14)

Page 14: CsF/Clinoptilolite: an Efficient Solid Base in SNAr · 2015-12-16 · 1" " CsF/Clinoptilolite: an Efficient Solid Base in S NAr and Copper-catalyzed Ullmann Reactions " Hoda Keipoura,b,

14  

 

1H-NMR spectrum 1,3-di-tert-butyl-2-(4-nitrophenoxy)benzene (Table 2,entry 14)

13C-NMR spectrum 1,3-di-tert-butyl-2-(4-nitrophenoxy)benzene (Table 2, entry 14)

Page 15: CsF/Clinoptilolite: an Efficient Solid Base in SNAr · 2015-12-16 · 1" " CsF/Clinoptilolite: an Efficient Solid Base in S NAr and Copper-catalyzed Ullmann Reactions " Hoda Keipoura,b,

15  

 

1H-NMR spectrum 1-(4-nitrophenoxy)naphthalene (Table 2, entry 15)

1H-NMR spectrum 1-(4-nitrophenoxy)naphthalene (Table 2, entry 15)

Page 16: CsF/Clinoptilolite: an Efficient Solid Base in SNAr · 2015-12-16 · 1" " CsF/Clinoptilolite: an Efficient Solid Base in S NAr and Copper-catalyzed Ullmann Reactions " Hoda Keipoura,b,

16  

 

1H-NMR spectrum 1-(4-nitrophenoxy)naphthalene (Table 2, entry 15)

13C-NMR spectrum 1-(4-nitrophenoxy)naphthalene (Table 2,entry 15)

Page 17: CsF/Clinoptilolite: an Efficient Solid Base in SNAr · 2015-12-16 · 1" " CsF/Clinoptilolite: an Efficient Solid Base in S NAr and Copper-catalyzed Ullmann Reactions " Hoda Keipoura,b,

17  

 

13C-NMR spectrum 1-(4-nitrophenoxy)naphthalene (Table 2,entry 15)

1H-NMR spectrum 1-nitro-2-(4-nitrophenoxy)benzene (Table 2, entry 17)

Page 18: CsF/Clinoptilolite: an Efficient Solid Base in SNAr · 2015-12-16 · 1" " CsF/Clinoptilolite: an Efficient Solid Base in S NAr and Copper-catalyzed Ullmann Reactions " Hoda Keipoura,b,

18  

 

1H-NMR spectrum 1-nitro-2-(4-nitrophenoxy)benzene (Table 2, entry 17)

13C-NMR spectrum 1-nitro-2-(4-nitrophenoxy)benzene (Table 2, entry 17)

Page 19: CsF/Clinoptilolite: an Efficient Solid Base in SNAr · 2015-12-16 · 1" " CsF/Clinoptilolite: an Efficient Solid Base in S NAr and Copper-catalyzed Ullmann Reactions " Hoda Keipoura,b,

19  

 

1H-NMR spectrum 1-nitro-3-(4-nitrophenoxy)benzene (Table 2, entry 18)

1H-NMR spectrum 1-nitro-3-(4-nitrophenoxy)benzene (Table 2, entry 18)

Page 20: CsF/Clinoptilolite: an Efficient Solid Base in SNAr · 2015-12-16 · 1" " CsF/Clinoptilolite: an Efficient Solid Base in S NAr and Copper-catalyzed Ullmann Reactions " Hoda Keipoura,b,

20  

 

13C-NMR spectrum 1-nitro-3-(4-nitrophenoxy)benzene (Table 2, entry 18)