Site-Selective Nitration of Aryl Germanes at Room Temperature

Dahiya, Amit; Gevondian, Avetik G.; Selmani, Aymane; Schoenebeck, Franziska

doi:10.1021/acs.orglett.3c02822

“…For instance, while CÀ N coupling for amination is yet to be achieved, nitration has been most recently accomplished via a presumed radical pathway. [51] Finally, while initial success in recovering and recycling the Ge-unit has been realized, further developments towards this goal will be welcome.…”

Section: Discussionmentioning

confidence: 99%

“…Therefore, new strategies that would widen the C–heteroatom bond‐forming capability of organogermanes would further enrich the scope and diversity of the amenable molecular scaffolds. For instance, while C−N coupling for amination is yet to be achieved, nitration has been most recently accomplished via a presumed radical pathway [51] . Finally, while initial success in recovering and recycling the Ge‐unit has been realized, further developments towards this goal will be welcome.…”

Section: Discussionmentioning

confidence: 99%

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

Rogova,

Ahrweiler,

Schoetz

et al. 2023

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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.

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

Rogova,

Ahrweiler,

Schoetz

et al. 2023

Angewandte Chemie

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0

View full text Add to dashboard Cite

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.

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Triply Selective & Sequential Diversification at C_sp³: Expansion of Alkyl Germane Reactivity for C−C & C−Heteroatom Bond Formation

Ahrweiler,

Schoetz,

Singh

et al. 2024

Angewandte Chemie

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We report the triply selective and sequential diversification of a single Csp3 carbon carrying Cl, Bpin and GeEt3 for the modular and programmable construction of sp3‐rich molecules. Various functionalizations of Csp3‐Cl and Csp3‐BPin (e.g. alkylation, arylation, homologation, amination, hydroxylation) were tolerated by the Csp3‐GeEt3 group. Moreover, the methodological repertoire of alkyl germane functionalization was significantly expanded beyond the hitherto known Giese addition and arylation to alkynylation, alkenylation, cyanation, halogenation, azidation, C‐S bond formation as well as the first demonstration of stereo‐selective functionalization of a Csp3‐[Ge] bond.

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Site-Selective Nitration of Aryl Germanes at Room Temperature

Cited by 8 publications

References 46 publications

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

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

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

Triply Selective & Sequential Diversification at C_sp³: Expansion of Alkyl Germane Reactivity for C−C & C−Heteroatom Bond Formation

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Site-Selective Nitration of Aryl Germanes at Room Temperature

Cited by 8 publications

References 46 publications

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

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

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

Triply Selective & Sequential Diversification at Csp3: Expansion of Alkyl Germane Reactivity for C−C & C−Heteroatom Bond Formation

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Triply Selective & Sequential Diversification at C_sp³: Expansion of Alkyl Germane Reactivity for C−C & C−Heteroatom Bond Formation