Synthesis and Reactivity of a Hydrido CNC Pincer Cobalt(III) Complex and Its
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1 Supporting Information Synthesis and Reactivity of a Hydrido CNC Pincer Cobalt(III) Complex and Its Application in Hydrosilylation of Aldehydes and Ketones Hongwei Zhou, Hongjian Sun, Shumiao Zhang and Xiaoyan Li * School of Chemistry and Chemical Engineering, Key Laboratory of Special Functional Aggregated Materials, Ministry of Education, Shandong University, Shanda Nanlu 27, Jinan, People s Republic of China * (X. Li): xli63@sdu.edu.cn. Table of contents 1. Proposed mechanism of formation of complex 1 page S2 2. Proposed mechanism of formation of complex 7 page S2 3. Ball-and-stick representation and Cartesian coordinates of complex 1 page S3 4. Table S1. Crystallographic Data for complexes 1, 2, 4 and 7 page S7 5. Stoichiometric reactions and NMR spectra page S8 6. IR, 1 H NMR, 31 P NMR and 13 C NMR spectra of complexes 1 7 page S H NMR spectra of alcohols page S26 S1
2 1. Proposed mechanism of formation of complex 1 Scheme S1 Proposed mechanism for the formation of complex 1 We proposed a mechanism for the formation of complex 1 (Scheme S1). The replacement of a trimethylphosphine ligand by the N atom of the ligand is the first step to afford intermediate A. According to the mechanism of formation of complex 4 from complex 1 and the result of the deuteration experiment it can be concluded that the next step for the formation of complex 1 should be the C H bond activation of the phenyl ring (ortho metalation). The cobalt(i) intermediate B was formed after elimination of methane. Complex 1 was produced via an intramolecular C H bond activation of the naphthyl C H bond. 2. Proposed mechanism of formation of complex 7 On the basis of the reactions of complex 1 with HCl and TFA (Scheme 2 and eq. (2)), a mechanism of formation of complex 7 is proposed in Scheme S2. As the reaction of complex 1 with HCl, complex 1 reacted with the acidic hydrogen of the enol form of acetylacetone to afford intermediate 7a. After reductive elimination between Co H and Co C(phenyl) bond 7a transformed into 7b with the imine group in π coordination. The S2
3 hydrido intermediate 7c was formed via C H bond activation of 7b. As the final product, complex 7 was produced by intermolecular insertion reaction of C=N bond into Co H bond. Scheme S2 proposed mechanism of formation of complex 7 3. Ball-and-stick representation and Cartesian coordinates of complex 1 Figure S1. Molecular structure of complex 1. Most of the hydrogen atoms are omitted for clarity. Selected information on bond lengths (Å) and angles (deg): Co1-H (6), Co1-N (4), Co1-C (5), Co1-C (5), Co1-P (2), Co1-P (2); C4-Co1-C (2), P1-Co1-P (7), N1-Co1-H (2), P1-Co1-H101 89(2), C4-Co1-H101 91(2). S3
4 Atomic coordinates ( x 10^4) of complex 1 U(eq) is defined as one third of the trace of the orthogonalized Uij tensor x y z U(eq) Co(1) 6922(7) 7159(5) 4564(4) 303(19) Co(2) 2261(7) 2836(8) 10299(5) 437(2) P(1) 5416(13) 7551(12) 5048(8) 348(3) P(2) 8137(15) 6333(12) 3981(8) 381(3) P(3) 1769(15) 1625(16) 11026(9) 455(4) P(4) 2493(2) 4402(19) 9820(12) 683(6) N(1) 7936(4) 8505(3) 4961(2) 298(8) N(2) 3394(10) 1918(8) 9818(5) 101(3) C(1) 5691(6) 8856(5) 5683(4) 453(13) C(2) 3891(6) 7725(7) 4339(4) 571(17) C(3) 5030(7) 6595(5) 5727(4) 508(15) C(4) 6175(5) 7993(5) 3611(3) 356(11) C(5) 5264(6) 7739(6) 2887(4) 457(14) C(6) 4864(6) 8513(7) 2285(4) 534(17) C(7) 5400(7) 9567(6) 2398(4) 532(16) C(8) 6350(6) 9895(5) 3120(4) 433(13) C(9) 6959(7) 10968(5) 3303(4) 513(16) S4
5 C(10) 7865(7) 11228(6) 4007(5) 543(17) C(11) 8261(6) 10448(5) 4603(4) 412(12) C(12) 7680(5) 9403(4) 4439(3) 332(10) C(13) 6733(5) 9085(4) 3708(3) 354(11) C(14) 8774(5) 8518(4) 5658(3) 324(10) C(15) 8822(5) 7487(4) 6055(3) 334(10) C(16) 9671(6) 7340(6) 6817(3) 438(13) C(17) 9624(7) 6329(6) 7155(3) 503(16) C(18) 8751(7) 5516(5) 6754(4) 495(16) C(19) 7917(6) 5663(5) 5989(4) 409(12) C(20) 7921(5) 6661(4) 5611(3) 320(10) C(21) 7733(8) 6273(6) 2874(4) 592(19) C(22) 8420(6) 4877(5) 4198(4) 439(13) C(23) 9711(7) 6961(6) 4244(4) 526(15) C(24) 151(7) 1533(9) 10992(5) 75(3) C(25) 2081(11) 217(7) 10739(5) 83(3) C(26) 2519(7) 1703(7) 12116(3) 527(16) C(27) 3845(7) 3164(9) 11132(6) 85(3) C(28) 4164(9) 3878(8) 11892(5) 75(3) C(29) 5381(8) 4042(8) 12435(5) 72(2) S5
6 C(30) 6297(8) 3495(7) 12225(5) 65(2) C(31) 6122(8) 2820(7) 11586(5) 66(2) C(32) 6968(8) 2224(7) 11356(5) 62(2) C(33) 6573(16) 1585(11) 10643(6) 136(6) C(34) 5512(9) 1417(9) 10100(6) 78(2) C(35) 4606(6) 2003(6) 10338(4) 484(14) C(36) 4816(8) 2689(7) 11016(5) 66(2) C(37) 2810(8) 1559(10) 9232(8) 95(4) C(38) 1534(10) 1625(8) 8793(4) 89(3) C(39) 932(9) 2334(8) 9340(5) 86(3) C(40) -306(11) 2530(11) 9039(7) 134(6) C(41) -1062(15) 2070(12) 8194(7) 121(5) C(42) -346(9) 1378(12) 7737(9) 128(6) C(43) 893(15) 1100(15) 7964(10) 156(7) C(44) 1141(10) 4978(9) 9106(7) 106(4) C(45) 3615(9) 4368(9) 9264(5) 88(3) C(46) 3026(10) 5591(8) 10533(6) 86(3) H(101) 627(5) 620(5) 418(4) 33(15) H(102) 151(5) 327(5) 1052(4) 30(14) S6
7 4. Table S1. Crystallographic Data for complexes 1, 2, 4 and empirical formula C 23 H 30 CoNP 2 C 23 H 29 CoINP 2 C 23 H 31 ClCoNP 2 C 28 H 38 CoNO 2 P 2 fw cryst syst Triclinic Trigonal Triclinic Monoclinic space group P-1 P-3 P-1 P2(1)/c a, Å (3) (3) (3) (5) b, Å (4) (3) (3) (4) c, Å (5) 8.829(2) (6) (6) β, deg (2) (3) (3) V, Å (12) (12) (7) (17) Z D x, g cm no. of reflns collected no. of unique data R int θ max, deg R 1 (I > 2σ(I)) wr 2 (all data) S7
8 5. Stoichiometric reactions and NMR spectra (1) Reaction of complex 1 with (EtO) 3 SiH In a NMR tube, complex 1 (25 mg, mmol) and (EtO) 3 SiH (10 mg, mmol) were dissolved in 0.6 ml of C 6 D 6. The NMR tube was sealed and placed in a 60 o C oil bath for 12 h. In the 1 H NMR spectrum, 4.71, 3.86 and 1.22 ppm are the signals of (EtO) 3 SiH, 4.71 ppm is the signal of SiH. The triplet at ppm is the signal of the hydrido ligand. In the 31 P NMR spectrum, a singlet at ppm is the signal of PMe 3 ligands. According to the 1 H NMR and 31 P NMR spectra, complex 1 does not react with (EtO) 3 SiH. S8
9 (2) Reaction of complex 1 with PhCHO In a NMR tube, complex 1 (33 mg, mmol) and PhCHO (8.3 mg, mmol) were dissolved in 0.6 ml of C 6 D 6. The NMR tube was sealed and placed in a 60 o C oil bath for 12 h. In the 1 H NMR spectrum, 9.72 ppm is the signal of CHO, a triplet at ppm is the signal of hydrido ligand. In the 31 P NMR spectrum, a singlet at ppm is the signal of PMe 3 ligands. According to the 1 H NMR and 31 P NMR spectra, complex 1 does not react with PhCHO. S9
10 S10
11 (3) Reaction of complex 1 with (EtO) 3 SiH and PhCHO In a NMR tube, complex 1 (37mg, mmol), PhCHO (8.9 mg, mmol) and (EtO) 3 SiH (14 mg, mmol) were dissolved in 0.6 ml of C 6 D 6. The NMR tube was sealed and placed in a 60 o C oil bath for 3 h. In the 1 H NMR spectrum, the signal of CHO at 9.72 ppm and the signal of SiH at 4.71 ppm disappeared. A singlet at 5.01 ppm is the single of CH 2 (PhCH 2 OSi(OEt) 3 ). In the 31 P NMR spectrum, a singlet at ppm is the signal of PMe 3 ligands. According to the 1 H NMR and 31 P NMR spectra, the reaction of complex 1 with (EtO) 3 SiH and PhCHO delivered only catalytic product and complex 1. 1 H NMR spectrum of reaction of complex 1 with (EtO) 3 SiH and PhCHO S11
12 6.IR, 1 H NMR, 31 P NMR and 13 C NMR spectra of complexes 1-7 (1) IR, 1 H NMR, 31 P NMR and 13 C NMR spectra of complex 1. Transmittance [%] IR spectrum (Nujol mull ) of complex 1. PMe 3 N Co H PMe complex Wavenumber cm-1 S12
13 S13
14 (2) IR, 1 H NMR, 31 P NMR and 13 C NMR spectra of complex 2 Transmittance [%] IR spectrum (Nujol mull ) of complex Wavenumber cm S14
15 S15
16 (3) IR, 1 H NMR, 31 P NMR and 13 C NMR spectra of complex 3 Transmi tta nce [%] IR spectrum (Nujol mull ) of complex 3 Br PMe 3 N Co PMe complex Wavenumber cm S16
17 S17
18 (4) IR, 1 H NMR, 31 P NMR and 13 C NMR spectra of complex 4 Transmitta nce [%] IR spectrum (Nujol mull) of complex PMe 3 N Co H Cl PMe 3 complex Wavenumber cm S18
19 S19
20 (5) IR, 1 H NMR, 31 P NMR and 13 C NMR spectra of complex 5 Transmitta nce [%] IR spectrum (Nujol mull ) of complex PMe 3 N Co H OCOCF 3 PMe 3 complex Wavenumber cm S20
21 S21
22 (6) IR, 1 H NMR, 31 P NMR spectra of complex 6 Reflecta nc e IR spectrum (Nujol mull ) of complex 6 H PMe 3 N Co Cl D PMe 3 complex Wavenumber cm S22
23 S23
24 (7) IR, 1 H NMR, 31 P NMR and 13 C NMR spectra of complex 7 Transmittance [%] IR spectrum (Nujol mull ) of complex 7 HN PMe 3 O Co O Me PMe 3 Me complex Wavenumber cm-1 S24
25 S25
26 7. 1 H NMR spectra (CDCl 3 ) of alcohols S26
27 S27
28 S28
29 S29
30 S30
31 S31
32 S32
33 S33
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