The development of efficient and sustainable methods for decarboxylative transformations is of great importance due to the ease of availability and nontoxicity of carboxylic acids. Despite tremendous efforts in this area, it remains challenging to develop enantioselective transformations direct from carboxylic acids. Herein we disclose a photoelectrocatalytic method for the direct and enantioselective decarboxylative cyanation. The photoelectrochemical reactions convert carboxylic acids to enantioenriched nitriles by employing cerium/copper relay catalysis with a cerium salt for catalytic decarboxylation and a chiral copper complex for stereoselective C-CN formation.

Photoelectrochemical Asymmetric Catalysis Enables Direct and Enantioselective Decarboxylative Cyanation.

Solid oxide fuel cells (SOFCs) are widely recognized as efficient energy sources that have the potential to shape the future of energy development. Among various types of SOFCs, the low-temperature operation of proton-conducting SOFCs (H–SOFCs) offers distinct advantages for wide commercialization compared to oxygen-ion conducting SOFCs (O–SOFCs). However, the commercialization of H–SOFCs is hindered by several challenges, including slow oxygen reduction kinetics and long-term instability of cathode materials. The electrochemical performance of the cathode system in H–SOFCs is limited by the poor proton conductivity of the cathode material and the scarcity of surface reaction sites. Additionally, the presence of undesirable phases induced by elements such as Cr and CO2 adversely affects the chemical stability and catalytic activity of the cathode. Thermal stress arising from the mismatch in coefficient of thermal expansion between the cathode and electrolyte further adds to the challenges. Therefore, this comprehensive review presents underlying mechanisms and potential solutions to overcome the challenges in H–SOFCs, leading to higher efficiency and wider commercialization of H–SOFCs. 

A comprehensive review of recent progresses in cathode materials for Proton-conducting SOFCs

The asymmetric difunctionalization of alkenes, a method transforming readily accessible alkenes into enantioenriched chiral structures of high value, has long been a focal point of organic synthesis. Despite tremendous efforts in this domain, it remains a considerable challenge to devise enantioselective oxidative dicarbofunctionalization of alkenes, even though these transformations can utilize stable and unfunctionalized functional group donors. In this context, we report herein a photoelectrocatalytic method for the enantioselective heteroarylcyanation of aryl alkenes, which employs unfunctionalized heteroarenes through C–H functionalization. The photoelectrochemical asymmetric catalysis (PEAC) method combines photoredox catalysis and asymmetric electrocatalysis to facilitate the formation of two C–C bonds operating via hydrogen (H2) evolution and obviating the need for external chemical oxidants. 

Photoelectrochemical Asymmetric Catalysis Enables Enantioselective Heteroarylcyanation of Alkenes via C-H Functionalization.

Contemporary photoelectrochemical strategies and reactions in organic synthesis.

We report a combination of electrocatalysis and photoredox catalysis to perform selective C(sp3)-H arylation/alkylation of alkanes, in which a binary catalytic system based on earth-abundant iron and nickel is applied. Reaction selectivity between two-component C(sp3)-H arylation and three-component C(sp3)-H alkylation is tuned by modulating the applied current and light source. Importantly, an ultra-low anodic potential (~0.23 V vs. Ag/AgCl) is applied in this protocol, thus enabling compatibility with a variety of functional groups (>70 examples). The robustness of the method is further demonstrated on a preparative scale and applied to late-stage diversification of natural products and pharmaceutical derivatives. 

Selective C(sp3)–H arylation/alkylation of alkanes enabled by paired electrocatalysis

Selective cleavage and functionalization of C-C bonds in alcohols is gaining increasing interest in organic synthesis and biomass conversion. In particular, the development of redox-neutral catalytic methods with cheap catalysts and clean energy is of utmost interest. In this work, we report a versatile redox-neutral method for the ring-opening functionalization of cycloalkanols by electrophotochemical (EPC) cerium (Ce) catalysis. The EPC-Ce-enabled catalysis allows for cycloalkanols with different ring sizes to be cleaved while tolerating a broad range of functional groups. Notably, in the presence of chloride as a counteranion and electrolyte, this protocol selectively leads to the formation of C-CN, C-C, C-S, or C-oxime bonds instead of a C-halide bond after β-scission. A preliminary mechanistic investigation indicates that the redox-active Ce catalyst can be tuned by electro-oxidation and photo-reduction, thus avoiding the use of an external oxidant. Spectroscopic characterizations (cyclic voltammetry, UV-vis, electron paramagnetic resonance, and X-ray absorption fine structure) suggest a Ce(III)/Ce(IV) catalytic pathway for this transformation, in which a Ce(IV)-alkoxide is involved.

Electrophotochemical Ce-Catalyzed Ring-Opening Functionalization of Cycloalkanols under Redox-Neutral Conditions: Scope and Mechanism.

A novel composite oxygen electrode: PrBaCo2O5+δ combined with negative thermal expansion oxide applied to reversible solid oxide cells

Correction: Diastereoselective synthesis of tetrahydrobenzo[b]azocines by Lu(OTf)3-catalyzed [4+4] cycloaddition of donor-acceptor cyclobutanes with anthranils.

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Electrophotochemical Ce-Catalyzed Ring-Opening Functionalization of Cycloalkanols under Redox-Neutral Conditions: Scope and Mechanism.

A novel composite oxygen electrode: PrBaCo2O5+δ combined with negative thermal expansion oxide applied to reversible solid oxide cells

Correction: Diastereoselective synthesis of tetrahydrobenzo[b]azocines by Lu(OTf)3-catalyzed [4+4] cycloaddition of donor-acceptor cyclobutanes with anthranils.