☆ 4.8 Review

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

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2023)

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Article Chemistry, Applied

Sulfonamide as Photoinduced Hydrogen Atom Transfer Catalyst for Organophotoredox Hydrosilylation and Hydrogermylation of Activated Alkenes

Kalu Ram Bajya et al.

Summary: Readily available, sterically, and electronically tunable sulfonamides have been developed as effective photoinduced hydrogen atom transfer (HAT) catalysts for selective Si-H functionalizations and hydrogermylation of activated alkenes. N-centered radicals, generated by photoredox catalyzed single-electron oxidation of sulfonamides, serve as key intermediates for silyl and germyl radical generation, enabling the synthesis of organosilicon and organogermanium compounds.

ADVANCED SYNTHESIS & CATALYSIS (2023)

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Article Chemistry, Multidisciplinary

Advances in Transition-Metal-Catalyzed Hydrogermylation of Alkenes and Alkynes

Zungui Zhao et al.

Summary: Hydrogermylation of alkenes and alkynes is a straightforward method for synthesizing organogermanium compounds, which have applications in organic synthesis, medicinal chemistry, and material science. This paper reviews the advances in transition-metal-catalyzed hydrogermylation of unsaturated carbon-carbon bonds, including alkenes, alkynes, dienes, and allenes, and aims to provide readers with an overview of the current status in this field. The progress, problems, and future perspectives are discussed.

CHINESE JOURNAL OF CHEMISTRY (2023)

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Article Chemistry, Multidisciplinary

cis-Selective Hydrogenation of Aryl Germanes: A Direct Approach to Access Saturated Carbo- and Heterocyclic Germanes

Akash Kaithal et al.

Summary: This study reports a catalytic approach to synthesizing cis-selective saturated carbo-and heterocyclic germanium compounds with a 3D framework through the hydrogenation of readily accessible aromatic germanes with a 2D framework. Nishimura's catalyst exhibited the best hydrogenation reactivity, achieving an isolated yield of up to 96%. The synthesized products showed versatile applications in coupling reactions and demonstrated orthogonal reactivity with boranes or silanes, acquiring a three-dimensional structure with high stability.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2023)

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Article Chemistry, Multidisciplinary

Orthogonal C-O Bond Construction with Organogermanes

Amit Dahiya et al.

Summary: We have developed a fully orthogonal C-O bond formation strategy by selectively coupling arylgermanes with alkyl alcohols (primary, secondary, and tertiary) as well as carboxylic acids. This method is tolerant to commonly used coupling handles and allows for rapid, air-tolerant, and mild C-O bond construction without the need for a base at room temperature.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2023)

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Article Chemistry, Organic

Enantio- and Regioconvergent Synthesis of γ-Stereogenic Vinyl Germanes and Their Use as Masked Vinyl Halides

Daniel Broesamlen et al.

Summary: A newly developed hept-4-yl-substituted Pybox ligand enables a nickel-catalyzed enantio- and regioconvergent alkylation of regioisomeric mixtures of racemic germylated allylic electrophiles with alkyl nucleophiles, yielding various chiral gamma-germyl alpha-alkyl allylic building blocks with excellent yields and enantioselectivities. The regioconvergence is attributed to the steering effect of the bulky germyl group. The resulting vinyl germanes can be easily halodegermylated without racemization of the allylic stereocenter, providing synthetically valuable gamma-stereogenic vinyl halides.

ORGANIC LETTERS (2023)

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Article Chemistry, Organic

Anti-Markovnikov Hydrogermylation of Alkenes via Lewis Acid Catalysis

Aymane Selmani et al.

Summary: The direct hydrogermylation of alkenes under Lewis acid catalysis using borane B(C6F5)3 as a catalyst is reported. It allows for a mild, metal-free hydrogermylation of alkenes and reduction of ketones and aldehydes simultaneously. Regardless of electronic biases, anti-Markovnikov hydrogermylation is achieved in high yields. Moreover, the process is scalable and can be conducted under mild conditions at room temperature.

SYNTHESIS-STUTTGART (2023)

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Article Chemistry, Physical

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

Haifeng Chen et al.

Summary: An efficient cobalt-catalyzed carbon-germanium bond formation method has been developed, providing access to a wide range of functionalized germane-containing compounds. This method shows a broad scope and good tolerance toward various functional groups, and is conducted under mild reaction conditions. Mechanistic studies shed light on the unexpected reaction pathway and sequential activation of different electrophiles.

ACS CATALYSIS (2023)

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Article Chemistry, Multidisciplinary

Base-Mediated Radio-Iodination of Arenes by Using Organosilane and Organogermane as Radiolabelling Precursors

Hugo Bloux et al.

Summary: Investigation of radio-iodination of arenes using ipso-electrophilic halogenation (IEH) from organosilane and organogermane precursors is performed. Discovery of a mild base mediated process enables radio-iodination in HFIP (1,1,1,3,3,3-hexafluoro-2-propanol) of aryl silane or germane, with germanes being more reactive. The clinical potential of arylgermanes as radio-iodination precursors is demonstrated through the labelling of [I-125]IMTO (iodometomidate) and [I-125]MIBG (meta-iodobenzylguanidine), providing an alternative to toxic precursors in radio-iododestannylation processes.

CHEMISTRY-A EUROPEAN JOURNAL (2023)

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Article Chemistry, Organic

Site-Selective Nitration of Aryl Germanes at Room Temperature

Amit Dahiya et al.

Summary: A site-selective ipso-nitration of aryl germanes is reported, which can also nitrate alternative functional handles in the presence of the germane.

ORGANIC LETTERS (2023)

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Article Chemistry, Multidisciplinary

Orthogonal Olefination with Organogermanes

Amit Dahiya et al.

Summary: A novel [Ge]-based oxidative Heck coupling reaction is reported, which allows for the site- and E-selective coupling of aryl germanes with alkenes. The reaction proceeds rapidly at room temperature and is tolerant of commonly used coupling handles and alternative functionalities.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2023)

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Article Chemistry, Multidisciplinary

Alkyl-GeMe3: Neutral Metalloid Radical Precursors upon Visible-Light Photocatalysis

Qing-Hao Xu et al.

Summary: The use of neutral metalloid compounds as radical precursors has played a significant role in the generation and reactions of alkyl radicals, particularly the successful application of alkylgermane compounds in nickel-catalyzed cross-coupling reactions.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

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Review Chemistry, Multidisciplinary

Inorganometallics (Transition Metal-Metalloid Complexes) and Catalysis

Bogdan Marciniec et al.

Summary: This Review summarizes the developments in inorganometallic catalysis over the last 15 years, highlighting the importance of inorganometallics in the synthesis of metalloid compounds and advanced organic synthesis.

CHEMICAL REVIEWS (2022)

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Article Chemistry, Organic

Hydrogermylation of Alkenes via Organophotoredox-Initiated HAT Catalysis

Adele E. Queen et al.

Summary: This method is a simple, metal-free approach that is tolerant of various functional groups in the hydro-germylation of olefins. The synthesized alkyl germanes exhibit high stability towards acidic, basic, or oxidizing conditions.

ORGANIC LETTERS (2022)

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Article Chemistry, Organic

Direct C-H Dehydrogenative Germylation of Terminal Alkynes with Hydrogermanes

Amit Dahiya et al.

Summary: A direct C(sp)-H germylation of terminal alkynes with triethyl germanium hydride was achieved. The method is simple and utilizes B(C6F5)3 catalyst combined with 2,6-lutidine as an organic base. Exclusive selectivity for dehydrogenative germylation of the alkyne over the competing hydrogermylation was observed.

ORGANIC LETTERS (2022)

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Article Chemistry, Organic

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

Peng Guo et al.

Summary: In this study, we reported a nickel-catalyzed reductive Csp(3)-Ge coupling of alkyl bromides with chlorogermanes, providing a facile access to organogermanes. The reaction tolerates various functionalities and can be applied to the modification of bioactive molecules.

ORGANIC LETTERS (2022)

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Article Chemistry, Physical

Modularity in the Csp3 Space-Alkyl Germanes as Orthogonal Molecular Handles for Chemoselective Diversification

Aymane Selmani et al.

Summary: This report investigates the potential of alternative functional handles, alkyl germanes, in modular coupling approaches for C-sp3 space synthesis. The chemoselective functionalization of alkyl germanes under photoredox conditions is demonstrated, allowing for selective diversification at different sites.

ACS CATALYSIS (2022)

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Article Chemistry, Physical

Cu-Catalyzed Enantioselective Hydrogermylation: Asymmetric Synthesis of Unnatural β-Germyl α-Amino Acids

Weidong Lin et al.

Summary: A copper-catalyzed asymmetric synthesis method has been developed to efficiently prepare chiral beta-germyl alpha-amino acid derivatives, and mechanistic studies have revealed the reaction process. Subsequent transformations yielded a series of germanium-containing functional molecules with potential utility.

ACS CATALYSIS (2022)

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Article Chemistry, Organic

Pd-Catalyzed Hydroxyl-Directed Cascade Hydroarylation/C-H Germylation of Nonterminal Alkenes and Aryl Iodides

Chun-Yan Wu et al.

Summary: Pd-catalyzed cascade hydroarylation and C-H germylation of nonterminal alkenes and aryl iodides have been achieved by hydroxyl assistance. The formation of a reactive oxo-palladacycle intermediate is the key step in the C-H germylation cascade, which is significantly suppressed by hydroxyl groups. The transformation exhibits excellent reactivity and selectivity for most substrates.

JOURNAL OF ORGANIC CHEMISTRY (2022)

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Article Chemistry, Physical

Orthogonal and Modular Arylation of Alkynylgermanes

Amit Dahiya et al.

Summary: This study unveils an efficient, mild, and modular arylation method of alkynylgermanes enabled by blue light-assisted gold catalysis, which has the potential to expand the modularity and scope in the construction of functional alkynes.

ACS CATALYSIS (2022)

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Article Chemistry, Multidisciplinary

A General Strategy for the Asymmetric Preparation of α-Stereogenic Allyl Silanes, Germanes, and Boronate Esters via Dual Copper Hydride- and Palladium-Catalysis

James Levi Knippel et al.

Summary: In this study, a general method for the enantioselective preparation of alpha-stereogenic allyl metalloids using dual CuH- and Pd-catalysis is reported. This approach allows access to enantioenriched allyl silanes, germanes, and boronate esters with broad functional group compatibility through a stereoretentive Cu-to-Pd transmetalation of an in situ generated alkyl copper species.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

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Article Chemistry, Multidisciplinary

Hydrogermylation initiated by trialkylborohydrides: a living anionic mechanism

Maciej Zaranek et al.

Summary: Sodium trialkylborohydrides were confirmed as selective catalysts for hydrogermylation of aromatic alkenes. Addition of phenylgermane and diphenylgermane in the presence of 10 mol% NaHB(sec-Bu)3 showed high selectivity, producing beta-germylated products, in contrast to the hydrosilylation process. DFT calculations supported the mechanism proceeding through a trisubstituted germanide anion attacking the terminal vinyl carbon.

CHEMICAL COMMUNICATIONS (2022)

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Review Chemistry, Organic

Organogermanium(iv) compounds in photo-induced radical reactions

Qing-Hao Xu et al.

Summary: This review summarizes the mechanism and applications of four types of organogermanium structures, including acylgermanes, hydrogermanes, tetraalkylgermanes, and digermanes, in photoinduced radical reactions. These compounds have great potential in modern radical systems.

ORGANIC CHEMISTRY FRONTIERS (2022)

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Review Chemistry, Multidisciplinary

Organothianthrenium salts: synthesis and utilization

Huan Meng et al.

Summary: Organothianthrenium salts are compounds containing a positively charged sulfur atom and a neutral sulfur atom. They have unique structural characteristics and chemical behaviors, making them attractive precursors for forming new C-C and C-X bonds. The thianthrenation strategy allows selective transformation of C-H, C-O, and other chemical bonds into organothianthrenium salts, providing a straightforward alternative for functionalization of different compounds.

CHEMICAL SCIENCE (2022)

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Article Chemistry, Multidisciplinary

Nickel-Catalyzed Reductive C-Ge Coupling of Aryl/Alkenyl Electrophiles with Chlorogermanes

Pei-Feng Su et al.

Summary: A novel cross-electrophile C-Ge coupling reaction has been reported, showing the potential of obtaining diverse organogermanes under mild conditions, with applications demonstrated in the synthesis and derivatization of complex molecules.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

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Article Chemistry, Physical

Regioselective Access to α-Vinylsilanes and α-Vinylgermanes by Cobalt-Catalyzed Migratory Hydrofunctionalization of 2-Alkynes

Manoj Kumar Sahoo et al.

Summary: This study demonstrates the regioselective migratory hydrofunctionalization of alkynes to produce alpha-vinylsilanes and alpha-vinylgermanes using a cobalt hydride based system. The mechanism of alkyne pi-bond migration by the cobalt hydride species is supported by both experimental and computational studies, which elucidates the unique alpha-vinyl selectivity.

ACS CATALYSIS (2021)

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Article Chemistry, Organic

Cobalt-Catalyzed (E)-β-Selective Hydrogermylation of Terminal Alkynes

Maxim R. Radzhabov et al.

Summary: A cobalt-catalyzed method has been developed for the hydrogermylation of alkynes, providing a selective and accessible route to (E)-beta-vinyl(trialkyl)germanes. The method demonstrates broad functional group tolerance and practical utility for late-stage hydrogermylation of natural products. Mechanistic studies support the syn-addition of Bu3GeH to an alkyne pi-complex.

ORGANIC LETTERS (2021)

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Article Chemistry, Organic

Synthesis of Dialkyl-Substituted Monofluoroalkenes via Palladium-Catalyzed Cross-Coupling of Alkyl Carbagermatranes

Chao Wang et al.

Summary: An unprecedented cross-coupling reaction of alkyl carbagermatranes with bromofluoroolefins was achieved to deliver dialkyl-substituted monofluoroalkenes, providing an opportunity for challenging molecules with excellent functional group tolerance. The utility of this strategy was demonstrated through the preparation of bioactive agent analogues, including antitubercular agent mimics and COX-2 inhibitor analogues, as well as late-stage fluoroalkenylation of drug-molecule derivatives.

ORGANIC LETTERS (2021)

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Article Chemistry, Organic

Base-Mediated Direct C-H Germylation of Heteroarenes and Arenes

Amit Dahiya et al.

Summary: The direct C-H germylation of heteroarenes, arenes, and benzylic C-H bonds using lithium tetramethylpiperidide (LiTMP) is a rapid and selective method that is operationally simple. This approach introduces newly accessed aryl germanes as viable coupling partners in Pd catalysis.

ORGANIC LETTERS (2021)

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Article Chemistry, Organic

Transition-Metal-Free, Formal C-H Germylation of Arenes and Styrenes via Dibenzothiophenium Salts

Aymane Selmani et al.

Summary: This study demonstrates a simple and selective germylation reaction at room temperature using a stable Ge source and dibenzothiophenium salts. Furthermore, it also successfully achieved the cross-coupling of newly made E-alkenyl germanes under air-tolerant nanoparticle catalysis, enabling chemoselective arylation.

ORGANIC LETTERS (2021)

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Review Chemistry, Multidisciplinary

Germatranes and carbagermatranes: (hetero)aryl and alkyl coupling partners in Pd-catalyzed cross-coupling reactions

Meng-Yu Xu et al.

Summary: Palladium-catalyzed cross-coupling reactions play a crucial role in the complex synthetic field. Our research group focuses on developing new germanium-based reagents and catalytic processes. Over the past three years, we have established new methods for the synthesis of novel compounds, with particular emphasis on the unique properties of alkyl carbagermatranes.

CHEMICAL COMMUNICATIONS (2021)

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Article Chemistry, Multidisciplinary

Tertiary cyclopropyl carbagermatranes: synthesis and cross-coupling

Shuo Yang et al.

Summary: The study focused on tertiary cyclopropyl carbagermatranes obtained through zinc-mediated decarboxylation, which showed efficient reactivity in palladium-catalyzed cross-coupling reactions. They also exhibited orthogonal reactivity with boron reagents, acting as robust nucleophiles for the synthesis of tertiary cyclopropane and efficient intermediates for quaternary center formation.

CHEMICAL COMMUNICATIONS (2021)

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Article Chemistry, Applied

Synthesis and Application of Heterocyclic Germatranes via Rhodium-Catalyzed Directed C-H Activation/Annulation with Alkynyl Germatranes and Palladium-Catalyzed Cross-Coupling

Meng-Yu Xu et al.

ADVANCED SYNTHESIS & CATALYSIS (2020)

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Article Chemistry, Multidisciplinary

Modular and Selective Arylation of Aryl Germanes (C-GeEt3) over C-Bpin, C-SiR3and Halogens Enabled by Light-Activated Gold Catalysis

Grant J. Sherborne et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

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Gold-Catalyzed Chemoselective Couplings of Polyfluoroarenes with Aryl Germanes and Downstream Diversification

Amit Dahiya et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

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Article Chemistry, Organic

Palladium-Catalyzed Disilylation and Digermanylation of Alkene Tethered Aryl Halides: Direct Access to Versatile Silylated and Germanylated Heterocycles

Marco Wollenburg et al.

ORGANIC LETTERS (2020)

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Orthogonal Stability and Reactivity of Aryl Germanes Enables Rapid and Selective (Multi)Halogenations

Christoph Fricke et al.

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Alkylation-Terminated Catellani Reactions Using Alkyl Carbagermatranes

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Ligand-Controlled Regiodivergent Palladium-Catalyzed Hydrogermylation of Ynamides

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Aymane Selmani et al.

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Organogermanes as Orthogonal Coupling Partners in Synthesis and Catalysis

Christoph Fricke et al.

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Alkyl Carbagermatranes Enable Practical Palladium-Catalyzed sp2-sp3 Cross-Coupling

Meng-Yu Xu et al.

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Visible-Light-Initiated Manganese-Catalyzed E-Selective Hydrosilylation and Hydrogermylation of Alkynes

Hao Liang et al.

ORGANIC LETTERS (2019)

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Gold-Catalyzed C-H Functionalization with Aryl Germanes

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ACS CATALYSIS (2019)

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ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

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Palladium-Catalyzed Catellani-Type Bis-silylation and Bis-germanylation of Aryl Iodides and Norbornenes

Weiwei Lv et al.

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Structure-Modified Germatranes for Pd-Catalyzed Biaryl Synthesis

Hai-Jie Song et al.

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Facile synthesis of unnatural -germyl--amino amides via Pd(ii)-catalyzed primary and secondary C(sp3)-H bond germylation

Zheng-Xin Zhou et al.

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Gold-Catalyzed Direct Oxidative Arylation with Boron Coupling Partners

Manuel Hofer et al.

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Access to Fully Alkylated Germanes by B(C6F5)3-Catalyzed Transfer Hydrogermylation of Alkenes

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Sebastian Keess et al.

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Experimental and Computational Studies on Remote γ-C(sp3)-H Silylation and Germanylation of Aliphatic Carboxamides

Arghya Deb et al.

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Visible-Light-Mediated Metal-Free Hydrosilylation of Alkenes through Selective Hydrogen Atom Transfer for Si-H Activation

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