Semi-Hydrogenation of Alkynes by a Tandem Photoredox System Free of Noble Metal
2021; Chinese Chemical Society; Volume: 4; Issue: 8 Linguagem: Inglês
10.31635/ccschem.021.202101457
ISSN2096-5745
AutoresYuan Tao, Shuwen Huan, Bingqing Ge, Sen Lin, Meifang Zheng, Xinchen Wang,
Tópico(s)Polyoxometalates: Synthesis and Applications
ResumoOpen AccessCCS ChemistryCOMMUNICATION5 Aug 2022Semi-Hydrogenation of Alkynes by a Tandem Photoredox System Free of Noble Metal Tao Yuan, Shuwen Huan, Bingqing Ge, Sen Lin, Meifang Zheng and Xinchen Wang Tao Yuan State Key Laboratory of Photocatalysis on Energy and Environment, College of Chemistry, Fuzhou University, Fuzhou 350116 , Shuwen Huan State Key Laboratory of Photocatalysis on Energy and Environment, College of Chemistry, Fuzhou University, Fuzhou 350116 , Bingqing Ge State Key Laboratory of Photocatalysis on Energy and Environment, College of Chemistry, Fuzhou University, Fuzhou 350116 , Sen Lin State Key Laboratory of Photocatalysis on Energy and Environment, College of Chemistry, Fuzhou University, Fuzhou 350116 , Meifang Zheng *Corresponding authors: E-mail Address: [email protected] E-mail Address: [email protected] State Key Laboratory of Photocatalysis on Energy and Environment, College of Chemistry, Fuzhou University, Fuzhou 350116 and Xinchen Wang *Corresponding authors: E-mail Address: [email protected] E-mail Address: [email protected] State Key Laboratory of Photocatalysis on Energy and Environment, College of Chemistry, Fuzhou University, Fuzhou 350116 https://doi.org/10.31635/ccschem.021.202101457 SectionsSupplemental MaterialAboutAbstractPDF ToolsAdd to favoritesDownload CitationsTrack Citations ShareFacebookTwitterLinked InEmail The selective hydrogenation reactions play a key role in industrial manufacture of fine chemicals, which mainly rely on noble metal catalysts. Herein, a noble-metal-free hybrid photosystem is established, in which boron carbonitride (BCN) and nickel bis-diphosphine complex (NiP) catalyze cooperatively the semi-hydrogenation of alkynes with high efficiency and excellent selectivity (>99%) under mild reaction conditions. In the process, BCN catalyst acts as an "electronic motor" and light harvester to establish the electron- and hydrogen-atom-delivery-transport chains to molecular NiP catalyst, with the ultimate output of reduced products. The work presents a photosystem that displays great potential for further organic transformations with high selectivity via cooperative organic photosynthesis. Download figure Download PowerPoint Introduction Selective hydrogenation ranks as one of the most important transformations for the construction of building blocks in the pharmaceutical, nutraceutical, and agrochemical industries.1–3 Nevertheless, the selective control of carbon–carbon double bond formation from a carbon–carbon triple bond remains a great challenge due to over-reduction or oligomerization.4 Up to now, a number of catalytic systems involving transition metals with the utilization of hydrogenating agents (e.g., H2 and NH3–BH3) have been reported for semi-hydrogenation reactions (Scheme 1a).5–9 One of the most prominent examples of alkyne to olefin hydrogenation is obtained by palladium (5 wt %) supported on calcium carbonate (Lindlar catalyst).10 Achievements by earth-abundant metals, such as Ni and Co, require elevated temperature as well as high H2 pressure (ca. 3 MPa) to accelerate kinetics or the addition of strong or toxic reducing agents, which limit their practical application in industrial manufacture.11–13 Therefore, a mild and cost-efficient protocol with mild energy input and an environmentally benign hydrogen source for selective hydrogenation of alkynes is of great interest to academic and industrial researchers. Scheme 1 | (a) Traditional catalytic hydrogenation of alkynes. (b) BCN-molecular nickel hybrid photosystem for semi-hydrogenation of alkynes. Download figure Download PowerPoint Sunlight provides sustainable energy to drive challenging chemical reactions with semiconductor materials through an environmentally friendly route.14–19 Substantial research efforts have mainly focused on promoting exciton dissociation of the semiconductors by means of textural tailoring, optical property optimization, and surface kinetic control.20–22 Recently, attention has been paid to hybrid photocatalysis, which accelerates charge separation by establishing electron transport chains between semiconductor and molecular catalyst, provides a feasible and efficient photocatalytic platform for continuous electron output to substrate, and is fully accessible to the toolbox of valuable organic synthesis.23–25 Among the nonmetal molecular catalysts, Ni-based complexes are highly available and possess tunable reactivity, providing a Ni–H intermediate for dihydrogen evolution or hydrogenation induced by heat or light.26–30 These advantages inspire hybrid photosystems that involve molecular nickel co-catalysts for the promising development of efficacious protocols for semi-hydrogenation by utilizing methanol/H2O and solar energy. Challenges remain in the construction of a robust and inexpensive catalyst platform that can efficiently couple proton reduction and electron transfer to molecular Ni catalytic cycle. Ceramic boron carbonitride (BCN), which is made up of earth-abundant and nontoxic elements (B, C, and N), has recently emerged as an attractive metal-free semiconductor for artificial photosynthesis.31–33 It exhibits much lower binding energy of excitons as well as faster charge migration and separation properties, thus possessing better electron-transport performance than other metal-free heterogeneous photocatalysts. BCN has been successfully applied to several important photochemical organic transformations.34–38 Herein, we report a BCN–Ni(dppp) (BCN–NiP) [dppp = 1,3-bis(diphenylphosphino)propane] hybrid system for visible-light-driven semi-hydrogenation of alkynes (Scheme 1b). In this strategy, BCN is synthesized by a pyrolysis method ( Supporting Information Scheme S1) and employed as a light harvester and "electronic motor", boosting kinetics of electron- and proton-transportation for target substrates. The cooperative system outputs excellent activities and selectivities of alkenes under ambient reaction conditions. Results and Discussion The study commenced with using diphenylacetylene (DPA, 1a) as the model hydrogenation substrate with developed BCN-molecular Ni cooperative photocatalytic system under blue light-emitting diode (LED) irradiation (Table 1 and Supporting Information Figure S1 and Table S1). The optimized yield was obtained with a 90% conversion of 1a and excellent semi-hydrogenation selectivity (>99%), using dppp as the ligand (Table 1, entry 1). Other semiconductors, such as mesoporous graphitic carbon nitride (mpg-CN), oxamide modified carbon nitride polymer (CN-OA-m), and CdS showed relatively low conversions or poor selectivity toward olefins (Table 1, entries 2–4, and Supporting Information Figure S2). The activity of cost-inefficient Ir(dtbbpy)(ppy)2PF6 was inferior to BCN as the photosensitizer, providing 2a in a yield of 40% (Table 1, entry 5). Trace amount of product was detected using H2 as the hydrogen source, indicating a transfer hydrogenation process from protic solvent instead of direct hydrogenation (Table 1, entry 6). Control experiments confirmed that BCN, NiCl2, dppp, and visible light were all important in our system, as rather low conversions were observed in the absence of those reaction components (Table 1, entries 7–10). Table 1 | Optimized Conditionsa Entry Variation of Standard Conditions Conv. (%)b Sel. for 2a (%)b Z:Eb 1 Standard conditions 90 >99 80:20 2 mpg-CN instead of BCN 55 >99 57:43 3 CN-OA-m instead of BCN 28 >99 68:32 4 CdS instead of BCN 98 18 28:72 5 Ir(dtbbpy)(ppy)2PF6 (1 mol %) instead of BCN 40 >99 88:12 6 H2 instead of H2O/CH3OH Trace — — 7 No BCN 4 >99 79:21 8 No NiCl2 6 >99 81:19 9 No dppp 8 >99 95:5 10 No light — — — aThe reactions were carried out with BCN (5 mg), 1a (0.1 mmol), NiCl2 (10 mol %), dppp (20 mol%), H2O (50 μL), CH3OH (50 μL), and THF (1 mL) under blue LED (3 W, λ = 455 ± 15 nm) irradiation for 48 h at 25 °C. bDetermined by gas chromatography mass spectrometry with acetophenone as internal standard. The spectroscopic characterizations were carried out to evaluate the optical and physical properties of the BCN-NiP system (Figure 1). As shown in Figure 1a, NiCl2 and dppp separately exhibited no absorption in the range of visible light, while the mixture exhibited the absorption peaks centered at 375 and 477 nm, which certified the in situ formation of NiP complex ( Supporting Information Figures S3 and S4). To get insight into the cooperative photosystem, the optical absorption of the reaction mixtures were tested along with prolonged illumination. Interestingly, the introduction of BCN photocatalyst led to the emergence of new absorbance features at 460, 570, and 650 nm, which indicated the formation of reactive nickel intermediates in the process (Figure 1b and Supporting Information Figures S5, S19, and S21). We also observed the formation of new singlets at 27.6 and 28.0 ppm in the 31P NMR spectrum of the reaction mixture after 5 h of illumination, which may arise from the generation of active nickel intermediates during the photocatalytic process ( Supporting Information Figure S6). As shown in photoluminescence (PL) spectra, the charge carrier recombination was suppressed with the addition of NiP complex, verifying the electron migration between BCN and NiP (Figure 1c). Furthermore, the BCN-NiP exhibited improved photocurrent (Figure 1d) and decreased Nyquist plots diameter ( Supporting Information Figure S7) in comparison with that of bare BCN, confirming the interfacial electron transfer process between BCN and NiP. Figure 1 | (a) UV–vis absorption spectra of NiCl2, dppp, and NiP. The samples were prepared in tetrahydrofuran (THF). (b) UV–vis absorption spectra of NiP at 0, 1, 3, and 5 h under blue LED illumination with and without BCN. Insert shows the color change of reaction mixture after illumination with a certain time. (c) PL spectra of BCN, BCN+NiP, and NiP in THF. (d) The periodic on/off photocurrent response of BCN and NiP/BCN. Download figure Download PowerPoint The performance of the BCN-NiP photosystem for transfer hydrogenation of 1a was thoroughly studied (Figure 2 and Supporting Information Figures S8 and S22). The amount of generated H2 was nearly 10 μmol in total, far less than that of semi-hydrogenation product 2a (Figures 2a and 2b and Supporting Information Figures S23 and S24). This outcome indicated that the hydrogenation rate of 1a was faster than H2 evolution rate. Minor amounts of 2a and H2 were observed in the absence of BCN (4% for 2a and 0.4 μmol for H2, respectively), which could arise from the in situ formation of molecular Ni–H species under light irradiation.28 Further assessment of the BCN–NiP hybrid photosystem was made under different wavelengths of incident light (Figure 2c). The yield of 2a declined upon red shift of the irradiation wavelength, implying a photocatalytic process. Obviously, the BCN–NiP photosystem still exhibited a considerable activity to produce 2a at the wavelength of 520 nm, which was due to the extensive light absorption of the BCN in the long-wavelength region. In addition, the reusability of the BCN was tested. The activity could be recovered after each cycle by adding NiCl2 and dppp (Figure 2d). Ni nanoparticles deposited on the surface of BCN is possible and may alter its photocatalytic properties.25,39 Structure and optical characterizations of the BCN materials before and after the reaction demonstrated the deposition of Ni nanoparticles and the stability of the BCN structure during prolonged light irradiation ( Supporting Information Figures S9–S13 and Table S2). When the recycled BCN material ([email protected]) was employed without adding extra molecular NiP complex, a minor yield of 2a was detected ( Supporting Information Figure S14). The experimental results support a BCN–NiP hybrid catalytic system. Figure 2 | (a) Yield of 2a over the course of this reaction, (b) the amount of H2 production during the photoreaction, and (c) wavelength-dependent yield of 2a with (w) and without (w/o) BCN semiconductor. (d) Recycle tests of BCN for the semi-hydrogenation of 1a. Sel., selectivity. Download figure Download PowerPoint The scope of alkyne derivatives was then explored to evaluate the versatility of the BCN–NiP hydrogenation system (Table 2). A broad range of aromatic substrates, containing electron-donating substituents such as methoxy, methyl, thio, phenyl, propyl, and ethoxy, were tolerated with moderate to excellent yields of alkenes ( 2a– 2k, up to 97%). 1l was reduced to 2l in 62% yield under the standard reaction condition. 1-Phenyl-1-propyne 1m afforded 2m in a 45% yield with >99% selectivity under higher-intensity light illumination. To note, an alkyne bearing ester group was also tolerated in this system and afforded 2n with a yield of 68% and excellent selectivity (>99%). Furthermore, N-heterocyclic and aliphatic alkenes ( 2o– 2q) were successfully produced from their corresponding alkynes in moderate to excellent yields. Our system was also suitable for the semi-hydrogenation of terminal alkynes, such as 1r, 1s, and 1t. The alkenes 2r, 2s, and 2t were obtained in general yields of 52%, 46%, and 43%, respectively. The above results demonstrated the good substituent tolerance and catalytic performance of the BCN–NiP photosystem for semi-hydrogenation of alkyne motifs. Furthermore, the BCN–NiP synergetic photosystem allowed gram-scale reaction, and 76% yield of 2a was obtained after 72 h blue light illumination ( Supporting Information Figure S15), paving the way for industrial manufacture. Table 2 | Scope of Alkynesa aThe reactions were carried out with BCN (10 mg), alkynes (0.2 mmol), NiCl2 (10 mol %), dppp (20 mol %), H2O (100 μL), CH3OH (100 μL), and THF (1 mL) under (3 W) 455 nm LEDs irradiation for 48 h at 25 °C. Selectivity (Sel.) for alkene was determined by gas chromatography mass spectrometry (GC-MS) and the yield was isolated yield. bThe yield and Z/E ratio were determined by GC-MS with biphenyl as internal standard. cThe reaction proceeded under (50 W) 420 nm LED illumination for 72 h. A series of control experiments were performed to shed light on the key mechanism of this photosystem (Figure 3). A radical capture test was conducted with 2,2,6,6-tetramethylpiperidinoxyl (TEMPO) as the trapping agent. The reaction stopped and radical-trapped adduct 4a was detected by high-performance liquid chromatography mass spectrometry (HPLC-MS), indicating the occurrence of a radical quenching process (Figure 3a and Supporting Information Figures S16 and S20). The phenomena also existed without the addition of NiCl2 and dppp ligand (Figure 3b). The above radical trapping experiments illustrated the formation of hydrogen radical initiated by the BCN photocatalyst ( Supporting Information Figure S25).40 In addition, the intensity of the TEMPO signals weakened during the light irradiation, suggesting the reduction of TEMPO to generate hydroxylamine (TEMPOH) by the active hydrogen species (Figure 3c).41,42 An E-enriched mixture of E -2a (Z/E = 20:80) was isomerized to a Z-enriched mixture (Z:E = 85:15) under the standard conditions, and the fully-hydrogenated product 3a was not detected ( Supporting Information Figure S17a). A similar result for the isomerization of E -2a was obtained in a bare BCN system without NiP ( Supporting Information Figure S17b), indicating that Z/E selectivity was irrelevant to molecular complex. The invariable deuterium content of olefin after isomerization demonstrated an energy transfer process mediated by the BCN photocatalyst ( Supporting Information Figures S17c and S18).43 The semi-hydrogenation selectivity is supported by density functional theory calculations ( Supporting Information Figures S26 and S27). It is attributed not only to the energy barrier that encumbers full hydrogenation of C=C bond, but also the proclivity to desorption of alkene over full hydrogenation to alkane. Figure 3 | Radical capture test for transfer hydrogenation of 1a by cooperative photosystem using TEMPO as a trapping agent with (a) and without (b) NiP. (c) Electron paramagnetic resonance spectra of active hydrogen species induced by BCN photocatalyst. Download figure Download PowerPoint Conclusion A tandem photoreduction system composed of BCN and molecular NiP co-catalyst has been established. The light-excited BCN semiconductor continuously transfers electrons and hydrogen species to the NiP catalyst to promote the reactivity of hydrogenation, while the NiP complex perfectly controls the selectivity during the prolonged photochemical operation. Because of the dual function of this unique photosystem, transfer hydrogenation of alkynes with high reactivity, excellent selectivity for alkenes, and good functional group tolerance is achieved under low-density blue LED irradiation. Such a synergetic strategy not only offers a new research perspective in design for selective photosynthesis of fine chemicals, but also expands the utilization of noble-metal-free semi-heterogeneous catalysis. Supporting Information Supporting Information is available and includes detailed experimental procedures and characterization data. Conflict of Interest There is no conflict of interest to report. Funding Information This work was financially supported by the National Natural Science Foundation of China (grant nos. 22071026, 21673040, 21961142019, 22032002, and U1905214), the National Key R&D Program of China (no. 2018YFA0209301), the Chang Jiang Scholars Program of China (no. T2016147), and the 111 Project (no. D16008). References 1. Chernichenko K.; Madarasz A.; Papai I.; Nieger M.; Leskela M.; Repo T.A Frustrated-Lewis-Pair Approach to Catalytic Reduction of Alkynes to Cis-Alkenes.Nat. Chem.2013, 5, 718–723. Google Scholar 2. Chinchilla R.; Najera C.Chemicals from Alkynes with Palladium Catalysts.Chem. Rev.2014, 114, 1783–1826. Google Scholar 3. Lin R. H.; Albani D.; Fako E.; Kaiser S. K.; Safonova O. V.; Lopez N.; Perez-Ramirez J.Design of Single Gold Atoms on Nitrogen-Doped Carbon for Molecular Recognition in Alkyne Semi-Hydrogenation.Angew. Chem. Int. Ed.2019, 58, 504–509. Google Scholar 4. Gorgas N.; Brunig R.; Stoger B.; Vanicek S.; Tilset M.; Veiros L. 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