ConspectusTransition-metal-catalyzed reductive coupling of electrophiles has emerged as a powerful tool for the construction of molecules. While major achievements have been made in the field of cross-couplings between organic halides and pseudohalides, an increasing number of reports demonstrates reactions involving more readily available, low-cost, and stable, but unreactive electrophiles. This account summarizes the recent results in our laboratory focusing on this topic. These findings typically include deoxygenative C-C coupling of alcohols, reductive alkylation of alkenyl acetates, reductive C-Si coupling of chlorosilanes, and reductive C-Ge coupling of chlorogermanes.The reductive deoxygenative coupling of alcohols with electrophiles is synthetically appealing, but the potential of this chemistry remains to be disclosed. Our initial study focused on the reaction of allylic alcohols and aryl bromides by the combination of nickel and Lewis acid catalysis. This method offers a selectivity that is opposite to that of the classic Tsuji-Trost reactions. Further investigation on the reaction of benzylic alcohols led to the foundation of a dynamic kinetic cross-coupling strategy with applications in the nickel-catalyzed reductive arylation of benzylic alcohols and cobalt-catalyzed enantiospecific reductive alkenylation of allylic alcohols. The titanium catalysis was later established to produce carbon radicals directly from unactivated tertiary alcohols via C-OH cleavage. The development of their coupling reactions with carbon fragments delivers new methods for the construction of all-carbon quaternary centers. These reactions have shown high selectivity for the functionalization of tertiary alcohols, leaving primary and secondary alcohols intact. Alkenyl acetates are inexpensive, stable, and environmentally friendly and are considered the most attractive alkenyl reagents. The development of reductive alkylation of alkenyl acetates with benzyl ammoniums and alkyl bromides offers mild approaches for the conversion of ketones into aliphatic alkenes.Extensive studies in this field have enabled us to extend the cross-electrophile coupling from carbon to silicon and germanium chemistry. These reactions harness the ready availability of chlorosilanes and chlorogermanes but suffer from the challenge of their low reactivity toward transition metals. Under reductive nickel catalysis, a broad range of alkenyl and aryl electrophiles couple well with vinyl- and hydrochlorosilanes. The use of alkyl halides as coupling partners led to the formation of functionalized alkylsilanes. The C-Ge coupling seems less substrate-dependent, and various common chlorogermanes couple well with aryl, alkenyl, and alkyl electrophiles. In general, functionalities such as Grignard-sensitive groups (e.g., acid, amide, alcohol, ketone, and ester), acid-sensitive groups (e.g., ketal and THP protection), alkyl fluoride and chloride, aryl bromide, alkyl tosylate and mesylate, silyl ether, and amine are tolerated. These methods provide new access to organosilicon and organogermanium compounds, some of which are challenging to obtain otherwise.

Reductive Cross-Coupling of Unreactive Electrophiles.

In the last decade, interfacial solar steam generation (ISSG), powered by natural sunlight garnered significant attention due to its great potential for low-cost and environmentally friendly clean water production in alignment with the global decarbonization efforts. In this review, we aim to share the knowledge and engage with a broader readership about the current progress of ISSG technology and the facing challenges to promote further advancements towards practical applications. The first part of this review assesses the current strategies for enhancing energy efficiency of ISSG systems, including optimizing light absorption, reducing energy losses, harvesting additional energy, and lowering evaporation enthalpy. Subsequently, we elucidate the current challenges faced by ISSG technologies, notably salt accumulation and bio-fouling issues in practical applications and discuss contemporary methods to overcome these challenges. In the end, we introduce potential applications of ISSG, ranging from initial seawater desalination and industrial wastewater purification to power generation, sterilization, soil remediation, and innovative concept of solar sea farm, highlighting the promising potential of ISSG technology in contributing to sustainable and environmentally conscious practices. Based on the review and in-depth understanding of these aspects, we propose the future research focuses to address potential issues in both fundamental research and practical applications. This article is protected by copyright. All rights reserved.

Interfacial Solar Evaporation: from Fundamental Research to Applications.

An efficient, electrochemically induced cobalt-catalyzed carbon–germanium bond formation provides access to a variety of functionalized germane-containing compounds, including aryl, vinyl, and alkyl germanes. The cobalt-catalyzed germylation is conducted under mild reaction conditions and exhibits a broad scope and functional group tolerance. Mechanistic experimental studies provide insight into the unexpected reaction pathway and the sequential activation of the different electrophiles. 

Carbon–Germanium Bond Formation via Low-Valent Cobalt-Catalyzed Cross-Electrophile Coupling

Within the sphere of traditional Pd0/PdII cross coupling reactions, organogermanes have been historically outperformed both in terms of scope and reactivity by more conventional transmetalating reagents. Subsequently, this class of compounds has been largely underutilized as a coupling partner in bond-forming strategies. Most recent studies, however, have shown that alternative modes of activation of these notoriously robust building blocks transform organogermanes into the most reactive site of the molecule - capable of outcompeting other functional groups (such as boronic acids, esters and silanes) for both C-C and C-heteroatom bond formation. As a result, over the past few years, the literature has increasingly featured methodologies that explore the potential of organogermanes as chemoselective and orthogonal coupling partners. Herein we highlight some of these recent advances in the field of organogermane chemistry both with respect to their synthesis and applications in synthetic and catalytic transformations.

Recent Developments with Organogermanes: their Preparation and Application in Synthesis and Catalysis.

Located between silicon and tin in the periodic table, organogermanium compounds have comparable abundant radical properties as well. According to earliear studies, various types of compounds such as acylgermanes, hydrogermanes,...

Organogermanium(IV) Compounds in Photo-Induced Radical Reactions

Nickel-Catalyzed Reductive Csp3-Ge Coupling of Alkyl Bromides with Chlorogermanes.

Conversion of solar energy into heat for water evaporation is of great significance to provide clean and sustainable technology for water purification by using inexhaustible sunlight. In this field, one of the challenges comes from the design of high-performance photothermal materials powerful in light harvesting, light-to-heat conversion, and water activation. Herein, it is demonstrated that rationalization of the ionic covalent organic framework (iCOF) can simultaneously satisfy these multiple requirements and a new iCOF STTP is constructed through the Schiff base chemistry in a rapid microwave-assisted solvothermal route by using a hydrophilic dye molecule safranineT as the ionic building block. The integrated dye-related ionic moieties greatly strengthen the light absorbance (>97%) throughout the entire solar spectrum from UV–vis to the infrared region. The framework ionic moieties provide strong polarization to reduce the exciton dissociation energy for enhanced photothermal effect, and in addition, promote sufficient water activation to decrease the water evaporation enthalpy. As an outcome, the STTP driven solar water evaporator affords a fast water evaporation rate of 3.55 kg h−1 m−2 and high solar-to-vapor efficiency of 95.8%. This study highlights the potential of designing iCOF materials for photothermal applications. 

Ionic Dye Based Covalent Organic Frameworks for Photothermal Water Evaporation

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Nickel-Catalyzed Reductive Csp3-Ge Coupling of Alkyl Bromides with Chlorogermanes.

Ionic Dye Based Covalent Organic Frameworks for Photothermal Water Evaporation