Selective Oxidation of Glycerol via Acceptorless Dehydrogenation Driven by Ir(I)-NHC Catalysts
Abstract
:1. Introduction
2. Results and Discussion
2.1. Synthesis and Characterization of bis-NHC Iridium(I) Complexes
2.1.1. Carbonylation of [Ir(cod){(MeIm)2CHCOO}]
2.1.2. Synthesis and Reactivity of [Ir(cod){(MeImCH2)2CHOH}]Br
2.1.3. Synthesis of [Ir(cod){(MeIm)2CH2}]I
2.1.4. Crystal and Molecular Structure of bis-NHC Iridium(I) Compounds
2.2. Synthesis and Characterization of NHC Iridium(I) Complexes
2.3. Dehydrogenation of Glycerol to Lactic Acid
3. Experimental Section
3.1. Materials and Methods
3.2. Scientific Equipment
3.3. Compound Synthesis
3.3.1. Synthesis of [Ir(CO)(cod){(MeIm)2CHCOO}] (2), Figure 5
3.3.2. Synthesis of [Ir(CO)2{(MeIm)2CHCOO}] (3), Figure 6
3.3.3. Synthesis of [Ir(cod){(MeImCH2)2CHOH}]Br (4), Figure 7
3.3.4. Synthesis of [Ir(CO)2{(MeImCH2)2CHOH}]Br (5), Figure 8
3.3.5. Synthesis of [Ir(cod){(MeIm)2CH2}]I (6), Figure 9
3.3.6. Synthesis of [IrCl(cod){MeIm(CH2)3OH}] (7), Figure 10
3.3.7. Synthesis of [Ir(cod){κ2C,O-{MeIm(CH2)3O}] (8), Figure 11
3.3.8. Synthesis of [Ir(cod){MeIm(CH2)3OH}2]Cl (9), Figure 12
3.4. General Procedure for the Acceptorless Dehydrogenation of Glycerol
3.5. Crystal Structure Determination
3.5.1. Crystal Data and Structure Refinement for 2
3.5.2. Crystal Data and Structure Refinement for 4
3.5.3. Crystal Data and Structure Refinement for 5
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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2 | 4 | 5 | |
---|---|---|---|
Ir–C(1) | 2.023(6) | 2.025(13) | 2.056(14) |
C(9)–Ir(1) | 2.089(6) | - | - |
C(25)–Ir(1) | 1.929(6) | - | - |
C(25)–O(26) | 1.139(7) | - | - |
Ir–C(11) | - | 2.011(12) | 2.083(13) |
Ir–C(17) | - | - | 1.876(14) |
Ir–C(19) | - | - | 1.883(15) |
Ir1–CT01 | 2.1679(2) | 2.0378(5) | - |
Ir1–CT02 | 2.0183(2) | 2.0708(5) | - |
C(17)–C(18) | 1.373(8) | 1.352(19) | - |
C(21)–C(22) | 1.446(8) | 1.391(18) | - |
C(14)–O(16) | 1.239(7) | - | - |
C(14)–O(15) | 1.245(7) | - | - |
C(17)–O(18) | - | - | 1.131(16) |
C(19)–O(20) | - | - | 1.151(17) |
C(1)–Ir(1)–C(11) | - | 84.1(5) | 80.4(5) |
C(1)–Ir(1)–C(9) | 83.6(2) | - | - |
CT01–Ir1–CT02 | 83.559(8) | 86.476(18) | - |
C1–Ir1–CT01 | 171.44(15) | - | - |
C25–Ir1–CT02 | 128.21(17) | - | - |
CT02–Ir1–C9 | 129.68(15) | - | - |
C(25)–Ir(1)–C(9) | 102.0(2) | - | - |
C(17)–Ir(1)–C(19) | - | - | 93.6(6) |
C(17)–Ir(1)–C(1) | - | - | 171.1(5) |
C(19)–Ir(1)–C(11) | - | - | 174.0(6) |
Entry | Catalyst | Base (mmol) | t [h] | T [°C] | Conv. [%] b | Select. LA(%) b | TONLA c |
---|---|---|---|---|---|---|---|
1 | 1 (1) | - | 66 | 115 | 0 | 0 | 0 |
2 | 4 (1) | - | 66 | 115 | 0 | 0 | 0 |
3 | - | KOH (5) | 66 | 115 | 0 | 0 | 0 |
4 | 3 (1) d | KOH (5) | 36 | 115 | 67 | 59 | 198 |
5 | 5 (1) d | KOH (5) | 36 | 115 | 69 | 76 | 262 |
6 | 1 (0.2) | KOH (5) | 2 | 130 | 24 | 93 | 112 |
7 | 3 (0.2) | KOH (5) | 2 | 130 | 30 | 98 | 147 |
8 | 4 (0.2) | KOH (5) | 2 | 130 | 61 | 93 | 284 |
9 | 5 (0.2) | KOH (5) | 2 | 130 | 91 | 92 | 419 |
10 | 6 (0.2) | KOH (5) | 2 | 130 | 15 | 100 | 75 |
11 | 7 (0.2) | KOH (5) | 2 | 130 | 80 | 86 | 344 |
12 | 8 (0.2) | KOH (5) | 2 | 130 | 35 | 98 | 172 |
13 | 9 (0.2) | KOH (5) | 2 | 130 | 56 | 92 | 258 |
14 | 7 e | NaOH (5) | 6 | 130 | 78 | 80 | 312 |
15 | 7 e | Cs2CO3 (5) | 25 | 130 | 23 | 84 | 97 |
16 | 1 (0.2) | KOH (5) | 0,75 | 150 | 31 | 93 | 144 |
17 | 3 (0.2) | KOH (5) | 0,75 | 150 | 40 | 94 | 188 |
18 | 4 (0.2) | KOH (5) | 0,75 | 150 | 71 | 92 | 327 |
19 | 5 (0.2) | KOH (5) | 0,75 | 150 | 100 | 93 | 465 |
20 | 7 (0.2) | KOH (5) | 0,75 | 150 | 70 | 92 | 322 |
21 | 5 (0.2) | KOH (0.5) | 0,75 | 150 | 15 | 59 | 44 |
22 | 5 (0.2) | KOH (2.5) | 0,75 | 150 | 80 | 57 | 228 |
23 | 5 (0.2) | KOH (6) | 0,75 | 150 | 91 | 91 | 414 |
24 | 5 (0.07) | KOH (5) | 24 | 150 | 91 | 71 | 923 |
25 | 5 (0.07) d | KOH (5) | 24 | 150 | 68 | 100 | 971 |
26 | 5 (0.07) | KOH (5) | 72 | 150 | 100 | 70 | 1000 |
27 | 5 (0.007) | KOH (5) | 72 | 150 | 74 | 100 | 10,571 |
28 | 5 (0.0014) | KOH (5) | 72 | 150 | 21 | 100 | 15,000 |
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Jiménez, M.V.; Ojeda-Amador, A.I.; Puerta-Oteo, R.; Martínez-Sal, J.; Passarelli, V.; Pérez-Torrente, J.J. Selective Oxidation of Glycerol via Acceptorless Dehydrogenation Driven by Ir(I)-NHC Catalysts. Molecules 2022, 27, 7666. https://doi.org/10.3390/molecules27227666
Jiménez MV, Ojeda-Amador AI, Puerta-Oteo R, Martínez-Sal J, Passarelli V, Pérez-Torrente JJ. Selective Oxidation of Glycerol via Acceptorless Dehydrogenation Driven by Ir(I)-NHC Catalysts. Molecules. 2022; 27(22):7666. https://doi.org/10.3390/molecules27227666
Chicago/Turabian StyleJiménez, M. Victoria, Ana I. Ojeda-Amador, Raquel Puerta-Oteo, Joaquín Martínez-Sal, Vincenzo Passarelli, and Jesús J. Pérez-Torrente. 2022. "Selective Oxidation of Glycerol via Acceptorless Dehydrogenation Driven by Ir(I)-NHC Catalysts" Molecules 27, no. 22: 7666. https://doi.org/10.3390/molecules27227666