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DOI: 10.1055/a-1990-5102
Sustainable and Mild Catalytic Acceptorless Dehydrogenations
This work is supported in part by the Japan Society for the Promotion of Science (JSPS) (KAKENHI) [Grant Nos. 22F22109 (M.K. and R.A.J.) and 22H04896 (M.K)].
Abstract
Catalytic acceptorless dehydrogenation of organic molecules plays a crucial role in fine-chemical synthesis as well as in energy storage and transport. In particular, the acceptorless dehydrogenation of saturated N-heteroarenes and hydrocarbons is realized by both transition-metal-free and transition-metal-catalyzed approaches. In this direction, our research group aims to develop mild catalytic acceptorless dehydrogenation protocols, in the main by using photoredox approaches. In this account, we briefly discuss the advances made by our group on the dehydrogenation of saturated N-heterocycles, aliphatic alcohols, and relatively challenging hydrocarbons.
1 Introduction
1.1 Challenges Associated with Catalytic Acceptorless Dehydrogenation
2 Transition-Metal-Free Dehydrogenation of N-Heterocycles
3 Photoinduced Hybrid-Catalysis-Enabled Dehydrogenations
3.1 The Binary Catalyst System
3.2 The Ternary Catalyst System
3.3 The Noble-Metal-Free Catalyst System
3.4 Catalytic Acceptorless Dehydrogenation of Aliphatic Alcohols
4 Self-Photo-Sensitizing Hydrogen Atom Transfer Catalysis
5 Summary
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Key words
catalytic acceptorless dehydrogenation - photoredox catalysis - hybrid catalysis - transition-metal catalysis - hydrogen atom transfer - heterocycles - hydrocarbons - alcoholsBiographical Sketches
Rahul A. Jagtap obtained his B.Sc. and M.Sc. degrees from S.R.T.M. University, Nanded, India. He received the Gold Medal from his university for securing 1st rank in his M.Sc. (organic chemistry). In 2021, he received his Ph.D. from CSIR-National Chemical Laboratory, Pune, India under the supervision of Prof. Benudhar Punji. Currently, he is working as a JSPS postdoctoral fellow with Prof. Motomu Kanai at The University of Tokyo, Japan. His research is focused on catalytic acceptorless dehydrogenations of alkanes.
Motomu Kanai received his bachelor’s degree from The University of Tokyo (UTokyo) in 1989 under the direction of the late Professor Kenji Koga. In the middle of his doctor’s course (in 1992), he obtained an assistant professor position in Professor Kiyoshi Tomioka’s group at Osaka University. He went on to complete his Ph.D. at Osaka University in 1995, before moving to the University of Wisconsin, USA, for postdoctoral studies with Professor Laura L. Kiessling. In 1997, he returned to Japan and joined Professor Masakatsu Shibasaki’s group at UTokyo as an assistant professor. After being a lecturer (2000–2003) and an associate professor (2003–2010), he became a full professor at UTokyo in 2010. He acted as a principal investigator of the ERATO Kanai Life Science Project (2011–2017) and was head investigator of MEXT Grant-in-Aid for Scientific Research on Innovative Areas, ‘Hybrid Catalysis’ (2017–2022). He has received the Pharmaceutical Society of Japan Award for Young Scientists (2001), the Thieme Journals Award (2003), the Merck-Banyu Lectureship Award (MBLA) (2005), the Asian Core Program Lectureship Award (2008 and 2010), the Thomson Reuters 4th Research Front Award (2016), the Nagoya Silver Medal (2022), and the Advanced Technology Award (2022). His research interest is directed towards catalysis development linking physical synthesis and life sciences.
Introduction
Non-renewable energy sources are depleting very rapidly and supplies may only be sufficient for a few more centuries at the current rate of energy consumption. Additionally, the threat of climate change may end the use of feedstock hydrocarbon deposits before the reserves are diminished. In this context, hydrogen gas has emerged as a green and environmentally attractive fuel because it is produced from renewable energy sources.[1] [2] [3] Hydrogen, as an energy source, has a wide range of applications and will contribute to a sustainable energy future as a carbon-emission-free fuel.[4] Considering the expansion of renewable energy sources, efficient methods to store and transport hydrogen will be of high interest. As hydrogen is gaseous under ambient conditions and diffuses easily, its transportation and storage are long-standing challenges.
The use of liquid organic hydrogen carriers (LOHCs) has emerged as a suitable approach to store and transport hydrogen in high density through dehydrogenation and hydrogenation cycles.[5] [6] [7] Considering the high importance of catalytic acceptorless dehydrogenation (CAD) in energy storage and organic synthesis, this field has witnessed tremendous attention.[8] The CAD process is challenging since the desaturation of organic molecules is unfavorable in terms of enthalpy. As a result, many of the acceptorless dehydrogenation protocols require harsh reaction conditions like high temperatures and prolonged reaction times. Additionally, the frequent use of less abundant noble transition metals limits the practical utility of precedented approaches. In this context, our group is constantly working to devise the mild catalytic acceptorless dehydrogenation of small organic molecules to achieve a practical approach to accessing green hydrogen. This account highlights the modern approaches for acceptorless dehydrogenations by transition-metal-free and photoinduced transition-metal catalysis.
1.1Challenges Associated with Catalytic Acceptorless Dehydrogenation
The hydrogenation/acceptorless dehydrogenation cycle under ambient conditions with a low energy cost is the foremost criterion for successful LOHCs. Reaction enthalpies are the critical factor for reactivity; e.g., the hydrogenation of benzene or toluene is exothermic and thermodynamically favorable (ΔH = –68 kJ/mol H2), whereas acceptorless dehydrogenation is an endothermic process and thus requires high reaction temperatures (64–69 kJ/mol H2) (Scheme [1]).[6] [9] [10] This physicochemical profile appeals to the development of efficient catalysts to overcome the thermodynamic barriers for acceptorless dehydrogenation.
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# 2
Transition-Metal-Free Dehydrogenation of N-Heterocycles
Catalytic acceptorless dehydrogenations of N-heterocycles are gaining considerable attention due to their feasible kinetics, thermodynamics, and reversibility in (de)hydrogenation.[11] To achieve CAD of N-heterocycles, both noble-transition-metal (Ir, Ru, Pd)[12] [13] [14] and base-metal (Fe, Co)[14–17] catalysts have been studied; however, these protocols often require harsh reaction conditions or sophisticated ligands around the metal centers. These literature precedents encouraged us to develop environmentally benign protocols for the dehydrogenation of N-heterocycles.
In 2016, we developed a borane-catalyzed, metal-free acceptorless dehydrogenation of saturated N-heterocycles.[18] At the same time, Grimme, Paradies, and co-workers reported similar conditions.[19] The basic idea is the reverse reaction of frustrated Lewis pair (FLP)-catalyzed hydrogenation of imines.[20] [21] [22] Thus, we hypothesized that hydride can be abstracted from the corresponding amines using a borane catalyst, which leads to the generation of a borohydride intermediate, and subsequent hydrogen evolution via protonolysis would allow the development of a unified acceptorless dehydrogenation process.
Extensive optimization studies revealed that tris(pentafluorophenyl)borane is the best catalyst and p-xylene is the solvent of choice at 150 °C (Scheme [2]). Under the optimal conditions, N-heteroarenes containing diverse functional groups such as alkyl, aryl, and halide are tolerated. It is important to note that the Lewis basic thioether group is well tolerated, which is otherwise sensitive to oxidative conditions. The substrate scope is also extended to partially saturated heterocycles. Heteroarenes such as thiazoles, indoles, and pyrazoles are accessed under the optimized reaction conditions. Furthermore, we have demonstrated the synthetic utility of the presented protocol by the synthesis of an intermediate for a mitochondria-targeted O2 probe. Due to the FLP mechanism, α-substituents relative to the nitrogen atom are prerequisites for the reaction to proceed. Although this protocol represents the first example of transition-metal-free acceptorless dehydrogenation, it requires a high reaction temperature. The limitation with high temperature has been further addressed by our group and many other research groups by merging with photoredox chemistry.
# 3
Photoinduced Hybrid-Catalysis-Enabled Dehydrogenations
Photoredox chemistry[23] has gained rapid interest in acceptorless dehydrogenation reactions over the past decades. This increased interest is due to the facile access of open-shell, highly reactive intermediates that are contrarily difficult to generate using traditional chemical methods.[24] Such photoredox approaches allow us to develop challenging dehydrogenations under milder reaction conditions by following low-energy barrier intermediates. Considering the advantages of photoredox reactions and earlier studies,[25] [26] [27] [28] [29] [30] [31] our group envisioned the development of mild, photoinduced catalytic dehydrogenations.
The Binary Catalyst System
The binary hybrid catalyst system was established to accomplish room-temperature acceptorless dehydrogenation of N-heterocycles (Scheme [3]).[32] First, single-electron transfer (SET) from the N-heterocycle to an exited photocatalyst (*PC+) results in an aminyl radical, which combines with a metal catalyst (Mn) to generate the oxidized metal amide intermediate (Mn+1). The oxidized metal amide intermediate is reduced by the photocatalyst (PC) to generate the reduced metal amide, which upon subsequent β-hydride elimination results in a metal hydride species (Mn–H) and an imine. This generated Mn–H species can evolve hydrogen gas by reacting with the proton generated during the photoredox step. Repeating this cycle from the imine will generate the N-heteroaromatic product and another mole of hydrogen gas.
Based on the proposed pathway, we have optimized CAD from various azacycles (Scheme [4]). Among the screened photocatalysts and metal salt catalysts, an acridinium photoredox catalyst and Pd(BF4)2·4MeCN catalyst were found to be the best along with KSbF6 as an additive. The reactions were performed at room temperature under blue light (430 nm). Adopting the optimized reaction conditions, a variety of substituted tetrahydroisoquinolines and indolines were efficiently dehydrogenated. A variety of electron-donating and electron-withdrawing substituents are tolerated, providing high yields of the desired products. Along with our report, Li[33] and Balaraman[34] independently reported a method for acceptorless dehydrogenation of heterocycles under dual catalytic conditions by merging cobalt catalysis with a photocatalyst. Despite noteworthy improvements to achieve the CAD process using a binary catalyst system, the demanding dehydrogenation of saturated hydrocarbons is still a challenging task.[34] [35] [36] [37]
# 3.2
The Ternary Catalyst System
Compared to the dehydrogenation of N-heterocycles, the CAD of saturated hydrocarbons is challenging but important in terms of the H2 storage strategy. The research group of Beller reported the light-driven, rhodium-catalyzed dehydrogenation of hydrocarbons with considerable turnover numbers (TONs).[30] [31] Further, Sorenson and co-workers reported on a noble-metal-free method for CAD of unactivated aliphatic and cyclic hydrocarbons in low to moderate yields.[38] We attempted CAD of tetrahydronaphthalene derivatives, which can be considered as model substrates for LOHCs. The attempts using a binary catalytic system failed to dehydrogenate tetrahydronaphthalenes; the probable reason was the inability of the photocatalysts to generate a carbon-centered radical. Therefore, we turned our attention to hybridizing the third catalyst to generate the benzyl radical (Scheme [5]).[32] We propose a sulfur-atom-containing organocatalyst that would generate a RS• radical and subsequently produce the benzyl radical efficiently through homolytic cleavage of the C–H bond. The probable working mode for the ternary hybrid catalyst system is shown in Scheme [5].
Based on the proposed mechanism, we have investigated thiol-containing organocatalysts. Among the screened organocatalysts, thiophosphoric imide was suitable in combination with the acridinium photoredox catalyst and Pd(BF4)2·4MeCN (Scheme [6a]). A variety of sensitive functional groups such as COMe, COOMe, and CONH t Bu are tolerated, providing good product yields. Furthermore, the allylic C–H activation followed by CAD is feasible under a ternary catalytic system (Scheme [6b]). Dehydrogenation of 3-methylcyclohexene provided toluene in 17% yield, which demonstrates the potential of the ternary hybrid catalyst system for applications in room-temperature CAD from LOHCs containing higher hydrogen/molecular weight ratios.
# 3.3
The Noble-Metal-Free Catalyst System
Photoinduced catalytic acceptorless dehydrogenation has witnessed significant development using environmentally deleterious precious noble-transition-metal catalysts. In sharp contrast, the use of earth-abundant and low-cost 3d transition metals is underdeveloped;[39] this may be due to the low stability of organometallic intermediates compared to their noble-transition metal counterparts. Furthermore, the exceptionally high reactivity of 3d metals leads to the formation of undesired products, and thus controlling the reactivity is a challenging task. This reactivity is often controlled by a suitable ligand backbone around these metals.[40] Among the first-row transition metals, nickel is an indispensable metal of choice considering its high natural abundance and low cost.[41] Compared to its late-transition metal counterparts in group 10, nickel catalysts demonstrate different reactivity modes involving variable oxidation states (NiI, NiII, NiIII, and NiIV) that are capable of easily interrupting carbon-centered radicals.[41] [42]
In 2018, our group was successful in establishing a ternary catalytic system comprising a nickel salt as a metal complex catalyst, thiophosphoric acid (TPA) as an organocatalyst, and an acridinium salt as a photoredox catalyst for the challenging dehydrogenation of hydrocarbons (Scheme [7]).[43] Comprehensive optimization studies revealed that Ni(NTf)2 (2.5 mol%), TPA (5 mol%), and the acridinium catalyst (5 mol%) were the best combination. Various tetrahydronaphthalene derivatives were successfully dehydrogenated in good to excellent yields, and functionalities such as halide, OAc, and Bpin were tolerated in satisfactory yields. Furthermore, we were successful in the dehydrogenation of 3-methylcyclohexene in a higher yield compared to the previous Pd-catalyzed system, which highlights the uniqueness of this method. The dehydrogenation of 4-methylcyclohexene and phenyl cyclohexane also gave moderate yields, suggesting that the ternary system will be applicable to substrates containing higher hydrogen content. The reported ternary hybrid catalysis that comprises an abundant nickel catalyst symbolizes an example of base-metal-catalyzed CAD of hydrocarbons. Following this report, Huang and co-workers reported a mild acceptorless dehydrogenation of diversely functionalized aliphatic substrates by a combination of organophotoredox and cobalt catalysis.[44]
# 3.4
Catalytic Acceptorless Dehydrogenation of Aliphatic Alcohols
The catalytic acceptorless dehydrogenation of alcohols is an attractive approach for practical applications as hydrogen storage systems and for the sustainable synthesis of fine chemicals.[1] [8] In recent years, transition-metal catalysts have been successfully demonstrated for CAD of alcohols. Because CAD of alcohols is a thermodynamically uphill process, however, high reaction temperatures (>100 °C) are usually required, which ultimately limits the practical applications.[45–47] Nevertheless, recent approaches manifest CAD of alcohols under visible light at room temperature. Despite remarkable progress, photoinduced CAD of alcohols was limited to only activated benzylic alcohols and CAD of aliphatic alcohols remained unexplored.[48–50] The major difficulties are the activation of aliphatic alcohols via hydrogen atom transfer (HAT) or an electron-transfer process, and the undue reactivity of α-oxy-carbon-centered radicals towards side reactions.
To address these issues, our group designed a ternary catalyst system that allows CAD of both aromatic and strenuous aliphatic alcohols at room temperature (Scheme [8]).[51] The catalyst system consisting of Ni(NTf)2·xH2O promoted the transformation in excellent yields. The use of Pd(BF4)2·4MeCN, instead of Ni(NTf)2·xH2O, showed lower reactivity, which emphasizes the unique reactivity of the nickel catalyst in CAD of alcohols. Furthermore, this method showcases the tolerance of a broad range of synthetically important functional groups, which includes access to the natural product epiandrosterone and the drug oxaprozin. The optimized process is applicable for large-scale reactions, even by reducing the catalyst loading to 0.5 mol%, highlighting the practical applications of the method in hydrogen evolution at room temperature.
Although this protocol is highly feasible for aliphatic secondary alcohols, the corresponding approach for primary alcohol CAD is not productive. The tentative reason may be that the product aldehydes contain a labile formyl C–H bond (BDE = 88.7 kcal/mol for benzaldehyde), which is reactive compared to the α-C–H bonds of the starting alcohol (96.1 kcal/mol for methanol) and thus inhibits the desired reaction via competing side reactions. To overcome this problem, we applied the ternary hybrid system to acceptorless cross-dehydrogenative coupling (ACDC) between aldehydes and alcohols to produce esters (Scheme [9]).
To understand the mechanism, we have performed preliminary mechanistic studies. Initially, a radical-trap experiment was conducted using 1 equivalent of TEMPO as a radical scavenger. The reaction was completely shut down and the starting alcohol was recovered, suggesting the formation of carbon-centered radicals. Further, to validate the assumption that desaturation occurs via β-hydride elimination, a reaction with benzhydrol, which does not contain a β-hydrogen atom, was performed. The reaction resulted in a poor yield, whereas the substrate dicyclohexylmethanol gave a 72% yield. These experiments suggest that desaturation via β-hydride elimination is plausible. Additionally, to validate the intermediacy of an enol, we performed the reaction with a deuterated substrate and found H/D scrambling at the α-position. Overall, these experiments support the hypothesized mechanistic pathway (Scheme [10]).
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# 4
Self-Photosensitizing Hydrogen Atom Transfer Catalysis
The hydrogen atom transfer (HAT) process is the key eliminatory step in many photochemical C–H functionalizations, which is responsible for substrate activation via electron transfer.[52] [53] The construction of catalytic HAT-active radicals primarily depends on SET from closed-shell molecules to excited photoredox catalysts.[24] Considerable efforts have been made by many research groups to establish efficient HAT catalysts and to study their applications in challenging organic reactions.[54–64] We have realized the importance of HAT catalysts by activating the relatively challenging C(sp3)–H bond (BDE = 80–95 kcal/mol) followed by acceptorless dehydrogenations. Alternatively, photoinduced electron transfer (PET) within an electron donor–acceptor (EDA) complex emerged as a potential and energy-saving substitute.[65] [66] [67] [68] [69] Considering the growing importance of EDA complexes and their applications, we have reported on an efficient photo-organocatalytic system for various C–H functionalizations and acceptorless dehydrogenation through the HAT process without using an additional photoredox catalyst.[70] We assumed the formation of a HAT-active radical via two-step SET processes (Scheme [11]), which is further supported by detailed mechanistic studies, including transient absorption studies, time-resolved EPR, and DFT studies. Optimization studies led us to identify that 7,7′-dimethoxy-substituted TPA was the best HAT catalyst precursor via EDA complexation.
The generality of the concept was demonstrated by four reaction types. First hydroxyalkylation of N-heteroaromatics was taken into account by facial cleavage of a formyl C–H bond (BDE = 88.7 kcal/mol for benzaldehyde) (Scheme [12]a). The reaction proceeded in good to excellent yields, including with substrates containing functionalities like halogen (F, Cl, Br) or ethers, and sterically congested substrates. Further, we achieved alkylation of N-heteroaromatics via cleavage of the α-oxy C–H bonds of alcohols (BDE = 94.8 kcal/mol for ethanol) in yields ranging from 54–94% and with broad substrate scope (Scheme [12]b).
Alcohol dehydrogenation is another challenging task to consider under the self-photosensitizing HAT system. As discussed above in Section 3.4, the potential HAT catalyst containing a thiyl radical plays a crucial role in alcohol dehydrogenation, and thus we decided to examine the EDA complex for CAD of alcohols. In this direction, we envisioned that photo-excitation of the EDA complex generates a HAT-active thiyl radical and an isoquinoline radical via PET (Scheme [13]). The generated thiyl radical abstracts a hydrogen atom from an alcohol substrate, leaving an α-oxy carbon radical, which further intercepts the nickel catalyst. Subsequent reduction of the Ni(III) intermediate by the isoquinoline radical and β-hydride elimination leads to formation of the corresponding ketones with the liberation of hydrogen gas after protonolysis of nickel hydride (Scheme [12c]). After the successful demonstration of three different catalytic systems, we achieved the activation of a benzylic C–H bond and addition to imines to access secondary amines (Scheme [12d]). The presented catalytic systems represent the potential of EDA complexes and encourage further development towards sustainable approaches.
# 5
Summary
The development of transition-metal catalysts for acceptorless dehydrogenation has significantly advanced in recent years. This account mainly highlights the progress in acceptorless dehydrogenation of heteroarenes, alcohols, and hydrocarbons by our group with transition-metal-free and transition-metal catalysts. The current developments uncover more opportunities for mild and efficient dehydrogenations using a combination of base-metal catalysts and organophotoredox chemistry. Although mild acceptorless dehydrogenation has gained considerable momentum, significant development is still needed in designing robust and efficient catalysts to overcome the current problems with the lower catalytic TON and TOF (turnover frequency). The applicability to substrates with the higher hydrogen density is also important. In this sense, catalysts that can dehydrogenate alkanes, such as methylcyclohexane or 1-(cyclohexylmethyl)-2-methylcyclohexane, under mild conditions are in high demand.[71] Furthermore, efforts to achieve low-cost and energy-efficient dehydrogenation processes using sunlight directly to contribute to hydrogen storage and transportation can be taken into account, which is the core of the hydrogen energy society.
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Conflict of Interest
The authors declare no conflict of interest.
Acknowledgment
We are grateful to all the past and present lab members and collaborators who have made the work described in this review possible. We also thank Harunobu Mitsunuma for reading this paper and providing important feedback.
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Corresponding Author
Publication History
Received: 05 November 2022
Accepted after revision: 30 November 2022
Accepted Manuscript online:
30 November 2022
Article published online:
03 January 2023
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References
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