College of Life Science, Dalian Nationalities University, Dalian , PR China.
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1 Electronic Supplementary Material (ESI) for New Journal of Chemistry. This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018 Postsynthetic modification of single Pd sites into uncoordinated polypyridine groups of a MOF as the highly efficient catalyst for Heck and Suzuki reactions Dapeng Dong, a Zhenghua Li, a Dedi Liu, a Naisen Yu, a Haiyan Zhao, a Huiying Chen* b Jia Liu a and Dongping Liu* a a Liaoning Key Laboratory of Optoelectronic Films and Materials, School of Physics and Materials Engineering, Dalian Nationalities University, Dalian , PR China. b College of Life Science, Dalian Nationalities University, Dalian , PR China. dongping.liu@dlnu.edu.cn; chy@dlnu.edu.cn Contents (1) Fig. S1 The IR spectra of HoMOF and Pd-HoMOF. (2) Fig. S2 IR spectra of HoMOF and Pd-HoMOF demonstrating the two weak Pd N stretching observed for Pd-HoMOF. (3) Fig. S3 The TG curve of HoMOF. (4) Fig. S4 The TG curve of PdHoMOF. (5) Fig. S5 Side view of one-dimensional chain along the b-axis for compound HoMOF. (6) Fig. S6 The XRD patterns after five reaction cycles of PdHoMOF. (7) Fig. S7 The 1 H NMR analysis for 2-TriPP-COOH. (8) Scheme S1 An illustrative sketch of proposed mechanism of the Suzuki Miyaura reaction of iodobenzene in the presence of Pd-HoMOF catalyst. (9) Table S1 Crystal data and structure refinement for compound HoMOF. (10) Table S2 Selected bond lengths (Å) and angles (º) for compound HoMOF. (11) Table S3 Reusability of Pd HoMOF catalyst in the Heck reaction. Reaction time = 1 h. (12) Table S4 Optimization of Suzuki Miyaura reaction. (13) Table S5 Reusability of Pd HoMOF catalyst in the Suzuki reaction. Reaction time = 1 h. (14) The results of GC-MS for the Heck reaction catalyzed by Pd HoMOF. (15) The results of GC-MS for the Suzuki Miyaura reaction catalyzed by Pd HoMOF.
2 (1) Transmittance (%) Wavenumber (cm -1 ) HoMOF Pd-HoMOF Fig. S1 The IR spectra of HoMOF and Pd-HoMOF. (2) Fig. S2 IR spectra of HoMOF (black) and Pd-HoMOF (red) demonstrating the two weak Pd N stretching observed for Pd-HoMOF.
3 (3) Fig. S3 The TG curve of HoMOF. (4) Fig. S4 The TG curve of PdHoMOF.
4 (5) Fig. S5 Side view of one-dimensional chain along the b-axis for compound HoMOF. (6) Intensity (degree) Fig. S6 The XRD patterns after five reaction cycles of Pd-HoMOF.
5 (7) Fig. S7 The 1 H NMR analysis for 2-TriPP-COOH.
6 (8) Scheme S1 An illustrative sketch of proposed mechanism of the Suzuki Miyaura reaction of iodobenzene in the presence of Pd-HoMOF catalyst.
7 (9) Table S1. Crystal data and structure refinement for compound HoMOF. formula C 66 H 42 HoN 9 O 6 Fw 1221 crystal system Space group 1 Monoclinic C2/c a, Å (2) b, Å (10) c, Å (9) β, (9) V, Å (7) Z 4 D c, g/cm (Mo K ), mm min, max, 2.226, no. total reflns no. uniq. reflns (R int ) 6113 (278) no. obs. [I 2 (I)] 5684 no. params 373 R1,wR2 [I 2 (I)] 275, 702 R1,wR2 (all data) 312, 716 GOF 83 R 1 = Σ ( F 0 F C ) / Σ F 0, wr 2 = [Σ w ( F 0 F C ) 2 / Σ w F 02 ] 1/2. (10) Table S2. Selected bond lengths (Å) and angles (º) for compound HoMOF. Ho(1)-O(3) (18) Ho(1)-O(1)# (2) Ho(1)-O(3)# (18) Ho(1)-N(4) 2.475(2) Ho(1)-O(2)# (2) Ho(1)-N(4)# (2) Ho(1)-O(2) 2.416(2) Ho(1)-N(5) 2.486(3) Ho(1)-O(1) 2.467(2) O(3)-Ho(1)-O(3)# (9) O(2)-Ho(1)-N(4) 66.86(7) O(3)-Ho(1)-O(2)# (8) O(1)-Ho(1)-N(4) (7) O(3)#1-Ho(1)-O(2)# (8) O(1)#1-Ho(1)-N(4) 74.85(7) O(3)-Ho(1)-O(2) 87.01(8) O(3)-Ho(1)-N(4)# (7) O(3)#1-Ho(1)-O(2) (7) O(3)#1-Ho(1)-N(4)# (6) O(2)#1-Ho(1)-O(2) 157(13) O(2)#1-Ho(1)-N(4)# (7) O(3)-Ho(1)-O(1) 79.13(7) O(2)-Ho(1)-N(4)# (8)
8 O(3)#1-Ho(1)-O(1) 74.24(7) O(1)-Ho(1)-N(4)# (7) O(2)#1-Ho(1)-O(1) (8) O(1)#1-Ho(1)-N(4)# (7) O(2)-Ho(1)-O(1) 52.84(7) N(4)-Ho(1)-N(4)# (9) O(3)-Ho(1)-O(1)# (7) O(3)-Ho(1)-N(5) (4) O(3)#1-Ho(1)-O(1)# (7) O(3)#1-Ho(1)-N(5) (4) O(2)#1-Ho(1)-O(1)# (7) O(2)#1-Ho(1)-N(5) 74(6) O(2)-Ho(1)-O(1)# (8) O(2)-Ho(1)-N(5) 74(6) O(1)-Ho(1)-O(1)# (11) O(1)-Ho(1)-N(5) 107(6) O(3)-Ho(1)-N(4) 88.65(6) O(1)#1-Ho(1)-N(5) 107(6) O(3)#1-Ho(1)-N(4) (7) N(4)-Ho(1)-N(5) 67(5) O(2)#1-Ho(1)-N(4) (8) N(4)#1-Ho(1)-N(5) 67(5) Symmetry transformations used to generate equivalent atoms for 1: #1: -x+1,y,-z+3/2. (11) Table S3. Reusability of Pd HoMOF catalyst in the Heck reaction. Reaction time = 1 h. Reaction Runs Yield (%) (12) Table S4. Optimization of Suzuki Miyaura reaction. a I + B(OH) 2 Solvent Cat Entry Base Solvent T( ) Time(h) Yield(%) b 1 KOH EtOH KOH H 2 O KOH Dioxane K 2 CO 3 DMF Cs 2 CO 3 DMF KOH DMF KOH DMF >99 8 KOH DMF >99 9 c KOH DMF none 10 d KOH DMF a Reaction conditions: Ph I ( mmol), phenylboronic acid (0.75mmol), base (1.5 mmol), Pd HoMOF (0.4 mol% Pd). b Yield determined by GC-MS analysis. c Parent HoMOF as the catalyst. d PdCl 2 (CH 3 CN) 2 as the catalyst (0.4 mol% Pd).
9 (13) Table S5. Reusability of Pd HoMOF catalyst in the Suzuki reaction. Reaction time = 1 h. Reaction Runs Yield (%) (14) The results of GC-MS for the Heck reaction catalyzed by Pd HoMOF 1. The results of GC (up) and MS (down) for iodobenzene and methyl acrylate 2.5 (x100,000) 1/ (x10,000) The results of GC (up) and MS (down) for 4-methyliodobenzene and methyl acrylate / / /120667/65562 (x10,000)
10 3. The results of GC (up) and MS (down) for 4-iodoacetophenone and methyl acrylate 6.0 1/ (x10,000) The results of GC (up) and MS (down) for 4-iodonitrobenzene and methyl acrylate (x10,000)
11 5. The results of GC (up) and MS (down) for iodobenzene and styrene (x100,000) 4.5 1/895449/ (x10,000) The results of GC (up) and MS (down) for 4-methyliodobenzene and styrene / / /120667/65562 (x10,000)
12 7. The results of GC (up) and MS (down) for bromobenzene and methyl acrylate (x100,000) / (x10,000) The results of GC (up) and MS (down) for 4-bromoacetophenone and methyl acrylate 2.5 2/ / (x10,000)
13 9. The results of GC (up) and MS (down) for 4-bromobenzaldehyde and methyl acrylate / / (x10,000) The results of GC for chlorobenzene and methyl acrylate 11. The results of GC for 4-methylchlorobenzene and methyl acrylate
14 12. The results of GC (up) and MS (down) for 4-chlorobenzaldehyde and methyl acrylate / / (x10,000) (15) The results of GC-MS for the Suzuki Miyaura reaction catalyzed by Pd HoMOF 1. The results of GC (up) and MS (down) for iodobenzene and phenylboronic acid / (x10,000) The results of GC (up) and MS (down) for 4-methyliodobenzene and phenylboronic acid
15 / (x10,000) The results of GC (up) and MS (down) for 4-methoxyiodobenzene and phenylboronic acid 7.5 1/ (x10,000) The results of GC (up) and MS (down) for 4-iodoacetophenone and phenylboronic acid 7.5 1/ (x10,000)
16 5. The results of GC (up) and MS (down) for 4-iodonitrobenzene and phenylboronic acid / (x10,000) The results of GC (up) and MS (down) for bromobenzene and phenylboronic acid 3.5 1/ (x10,000) The results of GC (up) and MS (down) for 4-methylbromobenzene and phenylboronic acid 1.5 2/ / /303755
17 (x10,000) The results of GC (up) and MS (down) for 4-methoxybromobenzene and phenylboronic acid 2/ / / (x10,000) The results of GC (up) and MS (down) for 4-bromobenzaldehyde and phenylboronic acid 1.25 (x10,000,000) 1/ (x10,000) The results of GC (up) and MS (down) for 4-bromoacetophenone and phenylboronic acid
18 (x10,000,000) / (x10,000) The results of GC (up) and MS (down) for chlorobenzene and phenylboronic acid 0 1/ (x10,000) The results of GC (up) and MS (down) for 4-methylchlorobenzene and phenylboronic acid / / / (x10,000) The results of GC (up) and MS (down) for 4-chlorobenzaldehyde and phenylboronic acid
19 (x10,000,000) 1.1 2/ / (x10,000)
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