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1 Supporting Information Dehydrogenation of Secondary Amines: Synthesis, and Characterization of Rare-Earth Metal Complexes Incorporating Imino- or Amido-Functionalized Pyrrolyl Ligands Qinghai Li, [a] Shuangliu Zhou,* [a] Shaowu Wang,* [a,b] Xiancui Zhu, [a] Lijun Zhang, [a] Zhijun Feng, [a] Liping Guo, [a] Fenhua Wang, [a] Yun Wei [a] [a] Laboratory of Functionalized Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials, College of Chemistry and Materials Science, Anhui ormal University, Wuhu, Anhui China [b] State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Shanghai , China. S1
2 Table 1. Crystallographic data for complexes 3a, 3b, 3c 3a 3b 3c empirical formula C 24 H 44 5 Si 4 Y C 24 H 44 5 Si 2 Dy C 24 H 44 5 Si 2 Yb formula weight T((K) 293(2) 293(2) 293(2) ( Å) crystal system Triclinic Triclinic Triclinic space group P 1 P 1 P 1 a (Å) (12) (9) (9) b (Å) (12) (9) (9) c (Å) (3) (2) (2) (deg) (2) (10) (10) (deg) (2) (10) (10) (deg) (2) (10) (10) V (Å 3 ) (4) (3) (3) Z D calcd (g cm -3 ) (mm -1 ) F(000) range (deg.) 2.06 to to to reflcns collcd/unique 13222/ / /6589 [R int = ] [R int = ] [R(int) = ] data/restraints/params 6612/579/ /579/ /567/497 Goodness of fit R 1 [I > 2 ( I)] wr largest diff. Peak and hole(e Å -3 ) and and and S2
3 Table 2. Crystallographic data for complexes 3d, 4a, 4b 3d 4a 4b empirical formula C 24 H 44 5 Si 2 Eu C 32 H 60 5 Si 2 Y C 32 H 60 Dy 5 Si 2 formula weight T((K) 293(2) 293(2) 293(2) ( Å) crystal system Triclinic Monoclinic Monoclinic space group P 1 C2/c C2/c a (Å) (11) (15) (18) b (Å) (11) (15) (19) c (Å) (2) (12) (16) (deg) (10) (deg) ( (10) (10) (deg) (10) V (Å 3 ) (3) (6) (7) Z D calcd (g cm -3 ) (mm -1 ) F(000) range (deg.) 2.04 to to to reflcns collcd/unique 14561/7754 [R(int) = ] 14518/3726 [R(int) = ] 14343/3717 [R(int) = ] data/restraints/params 7754 / 561 / /0/ /0/191 Goodness of fit R 1 [I > 2 ( I)] wr largest diff. Peak and hole(e Å -3 ) and and and S3
4 Table 3. Crystallographic data for complexes4c, 4c, 5 4c 4c 5 empirical formula C 32 H 60 Er 5 Si 2 C 43 H 72 ClErLi 2 6 O C 30 H 66 Li 4 6 Si 4 formula weight T((K) 293(2) 293(2) 293(2) ( Å) crystal system Monoclinic Monoclinic Monoclinic space group C2/c P2 1 /c P2 1 /n a (Å) (12) (14) (9) b (Å) (13) (3) (12) c (Å) (10) (3) (13) (deg) (deg) (10) (2) (10) (deg) V (Å 3 ) (5) (11) (3) Z D calcd (g cm -3 ) (mm -1 ) F(000) range (deg.) 1.74 to to to reflcns collcd/unique 14472/ / /4990 [R(int) = ] [R(int) = ] [R(int) = ] data/restraints/params 3703/0/ /196/ /0/208 Goodness of fit R 1 [I > 2 ( I)] wr largest diff. Peak and hole(e Å -3 ) and and and S4
5 Table 4. Crystallographic data for complexes 7a, 7b, 7c 7a 7b 7c empirical formula C 46 H 80 6 Si 4 d 2 C 46 H 80 6 Si 4 Sm 2 C 46 H 80 Er 2 6 Si 4 formula weight T (K) 293(2) 293(2) 293(2) (Å) crystal system Monoclinic Monoclinic Monoclinic space group C2/c C2/c P21/c a (Å) (5) (13) (5) b (Å) (3) (6) (4) c (Å) (4) (9) (3) (deg) (deg) (2) (10) (3) (deg) V (Å 3 ) 5545(2) (5) 5391(2) Z D calcd (g cm -3 ) (mm -1 ) F(000) range (deg.) 1.83 to to to reflcns collcd/unique 19673/ / /10566 [R int = ] [R int = ] [R int = ] data/restraints/params 5423/0/ /0/ /15/543 Goodness of fit R 1 [I > 2 ( I)] wr largest diff. Peak and hole(e Å -3 ) and and and S5
6 Figure 1. Molecular structure of the compound 3a, hydrogen atoms and disorder are omitted for clarity. Selected bond lengths (Å) and angles ( ): C(5A)-(2A) 1.282(6), C(5B)-(2B) 1.283(9), C(14A)-(4A) 1.288(6), C(14B)-(4B) 1.283(9), Y(1)-(1A) 2.303(4), Y(1)-(1B) 2.331(8), Y(1)-(2A) 2.420(5), Y(1)-(2B) 2.392(15), Y(1)-(3A) 2.318(4), Y(1)-(3B) 2.312(8), Y(1)-(4A) 2.433(4), Y(1)-(4B) 2.395(15), Y(1)-(5) 2.245(4), (2A)-C(5A)-C(4A) 123.2(6), (2B)-C(5B)-C(4B) 113.9(19), (4A)-C(14A)-C(13A) 122.5(5), (4B)-C(14B)-C(13B) 119.6(16). S6
7 Figure 2. Molecular structure of the compound 3b, hydrogen atoms and disorder are omitted for clarity. Selected bond lengths (Å) and angles ( ):(2A)-C(5A) 1.286(6), (2B)-C(5B) 1.289(9), (4A)-C(14A) 1.287(6), (4B)-C(14B) 1.285(9), Dy(1)-(1A) 2.332(7), Dy(1)-(1B) 2.33(2), Dy(1)-(2A) 2.439(4), Dy(1)-(2B) 2.458(11), Dy(1)-(3A) 2.345(9), Dy(1)-(3B) 2.301(17), Dy(1)-(4A) 2.453(4), Dy(1)-(4B) 2.419(12), Dy(1)-(5) 2.230(3), (2A)-C(5A)-C(4A) 123.0(5), (2B)-C(5B)-C(4B) 120.3(15), (4A)-C(14A)-C(13A) 122.9(5), (4B)-C(14B)-C(13B) 121.4(12). S7
8 Figure 3. Molecular structure of the compound 3c, hydrogen atoms and disorder are omitted for clarity. Selected bond lengths (Å) and angles ( ): (2A)-C(5A) 1.282(6), (2B)-C(5B) 1.282(8), C(14A)-(4A) 1.292(6), C(14B)-(4B) 1.282(8), Yb(1)-(1A) 2.271(6), Yb(1)-(1B) 2.294(11), Yb(1)-(2A) 2.407(4), Yb(1)-(2B) 2.354(9), Yb(1)-(3A) 2.277(7), Yb(1)-(3B) 2.332(16), Yb(1)-(4A) 2.389(4), Yb(1)-(4B) 2.405(9), Yb(1)-(5), 2.188(3), (2A)-C(5A)-C(4A) 122.5(5), (2B)-C(5B)-C(4B) 124.7(13), (4A)-C(14A)-C(13A) 122.0(5), (4B)-C(14B)-C(13B) 120.8(10). S8
9 Figure 4. Molecular structure of the compound 3d, hydrogen atoms and disorder are omitted for clarity. Selected bond lengths (Å) and angles ( ): (2A)-C(5A) 1.296(6), (2B)-C(5B) 1.294(9), C(14A)-(4A) 1.295(6), C(14B)-(4B) 1.292(9), Eu(1)-(1A) 2.374(10), Eu(1)-(1B) 2.40(3), Eu(1)-(2A) 2.482(4), Eu(1)-(2B) 2.491(14), Eu(1)-(3A) 2.387(7), Eu(1)-(3B) 2.38(3), Eu(1)-(4A) 2.491(4), Eu(1)-(4B) 2.417(15), Eu(1)-(5), 2.268(4), (2A)-C(5A)-C(4A) 122.9(6), (2B)-C(5B)-C(4B) 118.7(18), (4A)-C(14A)-C(13A) 123.0(5), (4B)-C(14B)-C(13B) 114.6(14). S9
10 Figure 5. Molecular structure of the compound 4a, hydrogen atoms are omitted for clarity. Selected bond lengths (Å) and angles ( ): Y(1)-(1) (19), Y (1)-(2) (19), Y (1)-(3) 2.240(2), C(9)-(2) 1.301(3), (3)-Y(1)-(1) 93.97(4), (3)-Y(1)-(2) (5), (1)-Y(1)-(2) 73.49(7), (1)-Y(1)-(1A) (9), (1)-Y(1)-(2A) (7), (2)-Y(1)-(2A) 96.61(9), (2)-C(9)-C(8) 124.4(2). S10
11 Figure 6. Molecular structure of the compound 4b, hydrogen atoms are omitted for clarity. Selected bond lengths (Å) and angles ( ): Dy(1)-(1) 2.421(2), Dy(1)-(2) (19), Dy(1)-(3) 2.232(3), C(9)-(2) 1.302(3), (3)-Dy(1)-(1) 94.14(4), (3)-Dy(1)-(2) (5), (1)-Dy(1)-(2) 73.12(7), (1)-Dy(1)-(1A) (9), (1)- Dy(1)-(2A) (7), (2)-Dy(1)-(2A) 96.13(9), (2)-C(9)-C(8) 124.6(2). S11
12 Figure 7. Molecular structure of the compound 4c, hydrogen atoms are omitted for clarity. Selected bond lengths (Å) and angles ( ): Er(1)-(1) 2.393(3), Er(1)-(2) 2.383(2), Er(1)-(3) 2.223(3), C(9)-(2) 1.311(4), (3)-Er(1)-(1) 93.68(6), (3)-Er(1)-(2) (6), (1)-Er(1)-(2) 73.94(9), (1)-Er(1)-(1A) (12), (1)-Er(1)-(2A) (9), (2)-Er(1)-(2A) 97.24(12), (2)-C(9)-C(8) 124.5(3). S12
13 Figure 8. Molecular structure of the compound 4c, hydrogen atoms are omitted for clarity. Selected bond lengths (Å) and angles ( ): Er(1)-(1) 2.346(3), Li(1)-(5) 2.040(8), Er(1)-(2) 2.458(3), Li(1)-(6) 2.044(8), Er(1)-(3) 2.300(3), Li(1)-O(1) 1.904(8), Er(1)-(4) 2.126(3), Cl(1)-Li(1) 2.442(8), Er(1)-Cl(1) (11), (3)- Li(2) 2.710(8), (2)-C(9) 1.278(5), C(18)-Li(2) 2.570(9), (4)-C(22) 1.458(5), C(19)-Li(2) 2.339(9), (6)-C(35) 1.285(6), C(20)-Li(2) 2.328(9), Li(2)-(5) 2.138(8), C(21)-Li(2) 2.566(9), C(34)-Li(2) 2.765(9), C(31)-Li(2) 2.771(9), (2)-C(9)-C(8) 124.1(4), C(22)-(4)-C(23) 115.3(3), (4)-C(22)-C(21) 111.2(3), C(22)-(4)-Er(1) 115.9(2), (6)-C(35)-C(34) 121.7(4), C(23)-(4)-Er(1) 128.8(3). S13
14 Figure 9. Molecular structure of the compound 5, hydrogen atoms are omitted for clarity. Selected bond lengths (Å) and angles ( ): Li(1)-(1) 2.057(4), Li(2)-(1A) 2.693(4), Li(1)-(2) 2.057(4), Li(2)-C(1A) 2.536(5), Li(1)-(3) 1.960(4), Li(2)-C(2A) 2.332(4), Li(2)-(1) 2.134(4), Li(2)-C(3A) 2.339(4), Li(2)-(3),2.064(4), Li(2)-C(4A) 2.553(4), C(5)-(2) 1.484(3), (2)-C(5)-C(4) (18). S14
15 Figure 10. Molecular structure of the compound 7a, hydrogen atoms are omitted for clarity. Selected bond lengths (Å) and angles ( ): d(1)-(1) 2.511(4), d(1)-(2) 2.259(4), d(1)-(3) 2.302(5), C(5)-(2) 1.451(7), d(1)-(1a) 2.791(5), d(1)-c(1a) 2.760(6), d(1)-c(2a) 2.816(6), d(1)-c(3a) 2.883(6), d(1)-c(4a) 2.880(6), d(1)-pyr 2.826(6), (1)-d(1)-(3) (16), (1)-d(1)-(2) 70.60(15), (1)-d(1)-(1A) 76.38(15), (2)-d(1)-(3) (17), (2)-d(1)-(1A) 97.68(15), (3)-d(1)-(1A) (16), (2)-C(5)-C(4) 112.3(5). d(1)-pyr means the average bond distances between neodymium ion and the pyrrolyl ring. S15
16 Figure 11. Molecular structure of the compound 7b, hydrogen atoms are omitted for clarity. Selected bond lengths (Å) and angles ( ): Sm(1)-(1) 2.472(2), Sm(1)-(2) 2.234(2), Sm(1)-(3) 2.278(2), C(5)-(2) 1.460(4), Sm(1)-(1A) 2.770(2), Sm(1)-C(1A) 2.725(3), Sm(1)-C(2A) 2.783(3), Sm(1)-C(3A) 2.851(3), Sm(1)-C(4A) 2.855(3), Sm(1)-Pyr 2.797(3), (1)-Sm(1)-(3) (8), (1)-Sm(1)-(2) 71.37(8), (1)-Sm(1)-(1A) 76.22(8), (2)-Sm(1)-(3) (8), (2)-Sm(1)-(1A) 98.17(8), (3)-Sm(1)-(1A) (8), (2)-C(5)-C(4) 112.3(2). Sm(1)-Pyr means the average bond distances between samarium ion and the pyrrolyl ring. S16
17 Figure 12. Molecular structure of the compound 7c, hydrogen atoms are omitted for clarity. Selected bond lengths (Å) and angles ( ): Er(1)-(1) 2.353(6), Er(1')-(1') 2.356(5), Er(1)-(2) 2.166(6), Er(1')-(2') 2.177(5), Er(1)-(3) 2.213(6), Er(1')-(3') 2.201(5), C(5)-(2) 1.467(9), C(5')-(2') 1.459(7), Er(1)-(1A), 2.728(6), Er(1')-(1'A) 2.701(5), Er(1)-C(1A) 2.643(8), Er(1')-C(1'A) 2.650(6), Er(1)-C(2A) 2.676(8), Er(1')-C(2'A) 2.711(7), Er(1)-C(3A) 2.807(7), Er(1')-C(3'A) 2.786(7), Er(1)-C(4A) 2.805(7), Er(1')-C4'A) 2.792(6), Er(1)-Pyr 2.732(8), Er(1')-Pyr 2.728(7), (2)-C(5)-C(4) 113.7(6), (2')-C(5')-C(4') 111.6(5). Er(1)-Pyr means the average bond distances between erbium ion and the pyrrolyl ring. S17
18 Copy of 1 H and 13 C MR spectra 1 H MR spectrum of compound 1 13 C MR spectrum of compound 1 S18
19 1 H MR spectrum of compound 1a 13 C MR spectrum of compound 1a S19
20 1 H MR spectrum of compound 2 13 C MR spectrum of compound 2 S20
21 1 H MR spectrum of compound 3a 13 C MR spectrum of compound 3a S21
22 D D t Bu t Bu t Bu t Bu Y (SiMe 3 ) 2 + t Bu D Y (SiMe 3 ) 2 + t Bu H Y (SiMe 3 ) 2 1 H MR spectra of compounds 3a and 3a D D t Bu t Bu t Bu t Bu Y (SiMe 3 ) 2 + t Bu D Y (SiMe 3 ) 2 + t Bu H Y (SiMe 3 ) 2 13 C MR spectra of compounds 3a and 3a S22
23 1 H MR spectrum of compound 4a 13 C MR spectrum of compound 4a S23
24 1 H MR spectrum of compound 5 13 C MR spectrum of compound 5 S24
25 1 H MR spectrum of compound 6 13 C MR spectrum of compound 6 S25
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Spain c Departament de Química Orgànica, Universitat de Barcelona, c/ Martí I Franqués 1-11, 08080, Barcelona, Spain.
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