Recent Developments with Organogermanes: their Preparation and Application in Synthesis and Catalysis DOI Creative Commons
Tatiana Rogova,

Eric Ahrweiler,

Markus D. Schoetz

и другие.

Angewandte Chemie, Год журнала: 2023, Номер 136(8)

Опубликована: Окт. 30, 2023

Abstract Within the sphere of traditional Pd 0 /Pd II cross coupling reactions, organogermanes have been historically outperformed both in terms scope and reactivity by more conventional transmetalating reagents. Subsequently, this class compounds has largely underutilized as a partner bond‐forming strategies. Most recent studies, however, shown that alternative modes activation these notoriously robust building blocks transform into most reactive site molecule—capable outcompeting other functional groups (such boronic acids, esters silanes) for C−C C–heteroatom bond formation. As result, over past few years, literature increasingly featured methodologies explore potential chemoselective orthogonal partners. Herein we highlight some advances field organogermane chemistry with respect to their synthesis applications synthetic catalytic transformations.

Язык: Английский

Recent Developments with Organogermanes: their Preparation and Application in Synthesis and Catalysis DOI Creative Commons
Tatiana Rogova,

Eric Ahrweiler,

Markus D. Schoetz

и другие.

Angewandte Chemie International Edition, Год журнала: 2023, Номер 63(8)

Опубликована: Окт. 30, 2023

Within the sphere of traditional Pd

Язык: Английский

Процитировано

26
meta-Nitration of Pyridines and Quinolines through Oxazino Azines DOI
Kuruva Balanna, Armido Studer

Journal of the American Chemical Society, Год журнала: 2025, Номер 147(9), С. 7485 - 7495

Опубликована: Фев. 24, 2025

meta-Nitration of azines (pyridines and quinolines) serves as a powerful method for the prompt construction derivatization several pharmaceuticals, agrochemicals, materials. However, due to inherent electronic properties pyridines, achieving direct selective meta-C-H nitration under mild conditions has been long-standing challenge in synthetic chemistry. Currently, there is no adequate strategy late-stage pyridine-containing drugs drug precursors. To address this void, we introduce practical protocol highly regioselective meta-nitration pyridines using dearomatization-rearomatization strategy. The introduced provides diversification platform at meta-position via radical pathway. This mild, open-air, one-pot, scalable, catalyst-free process employed pyridine containing drugs, precursors, ligands limiting reagents. Consecutive C3 C5 difunctionalization also achieved with complete regiocontrol relying on sequential addition, which further highlights potential presented work. Additionally, obtained products could be transformed into meta-amino azine other valuable building blocks. Incorporating N-heterocyclic amine structures through amidation ibuprofen significantly improved drug's clinical success, highlighting importance

Язык: Английский

Процитировано

2
Ipso-Nitration of Boronic Esters Enabled by Ferric Nitrate Nonahydrate (Fe(NO3)3·9H2O) in HFIP DOI

Yuzhu Zheng,

Zongyi Liu,

Qing Huang

и другие.

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Март 13, 2025

We describe in this work an operationally facile and generally applicable ipso-nitration of boronic esters by Fe(NO3)3·9H2O hexafluoroisopropanol (HFIP), allowing us fast access to various nitroarenes that are currently difficult obtain via traditional electrophilic C–H nitrations. In contrast previous deborylative ipso-nitrations, new protocol utilized less reactive more stable organoboron reagents therefore had significantly improved substrate scope functional group tolerance, which was exemplified the late-stage natural products, pharmaceuticals, biologically active molecules.

Язык: Английский

Процитировано

1
Triply Selective & Sequential Diversification at Csp3: Expansion of Alkyl Germane Reactivity for C−C & C−Heteroatom Bond Formation DOI Creative Commons

Eric Ahrweiler,

Markus D. Schoetz,

Gurdeep Singh

и другие.

Angewandte Chemie International Edition, Год журнала: 2024, Номер 63(16)

Опубликована: Фев. 22, 2024

Abstract We report the triply selective and sequential diversification of a single C sp 3 carbon carrying Cl, Bpin GeEt for modular programmable construction ‐rich molecules. Various functionalizations −Cl −BPin (e.g. alkylation, arylation, homologation, amination, hydroxylation) were tolerated by −GeEt group. Moreover, methodological repertoire alkyl germane functionalization was significantly expanded beyond hitherto known Giese addition arylation to alkynylation, alkenylation, cyanation, halogenation, azidation, C−S bond formation as well first demonstration stereo‐selective ‐[Ge] bond.

Язык: Английский

Процитировано

6
Electrochemistry-Enabled C-Heteroatom Bond Formation of Alkyl Germanes DOI

Markus D. Schoetz,

Kristina Deckers,

Gurdeep Singh

и другие.

Journal of the American Chemical Society, Год журнала: 2024, Номер 146(31), С. 21257 - 21263

Опубликована: Июль 26, 2024

Because of their robustness and orthogonal reactivity features, alkyl germanes bear significant potential as functional handles for the construction C(sp3)-rich scaffolds, especially in context modular synthetic approaches. However, to date, only radical-based has been accessible from these handles, which limits types possible decorations. Here, we describe first general C(sp3)–heteroatom bond formation (−GeEt3) by leveraging electrochemistry unlock polar reactivity. This approach allowed us couple C(sp3)–GeEt3 with a variety nucleophiles construct ethers, esters, amines, amides, sulfonamides, sulfides, well C–P, C–F, C–C bonds. The compatibility electrochemical strategy C1 motif was also showcased, involving sequential functionalization Cl, Bpin, ultimately GeEt3 via electrochemistry.

Язык: Английский

Процитировано

5
Photoinduced decarboxylative germylation of α-fluoroacrylic acids: Access to germylated monofluoroalkenes DOI

Xiao‐Yu Lu,

Yu-Jun Qian,

Hai‐Lun Sun

и другие.

Chemical Communications, Год журнала: 2024, Номер 60(51), С. 6556 - 6559

Опубликована: Янв. 1, 2024

Herein, a novel strategy is presented for the photoinduced decarboxylative and dehydrogenative cross-coupling of wide range α-fluoroacrylic acids with hydrogermanes. This methodology provides an efficient robust approach producing various germylated monofluoroalkenes excellent stereoselectivity within brief photoirradiation period. The feasibility this reaction has been demonstrated through gram-scale reaction, conversion monofluoroalkenes, modification complex organic molecules.

Язык: Английский

Процитировано

3
An efficient Cu catalyzed regioselective Ortho-nitration approach for the synthesis of 2-nitroarylcyanamides: Molecular docking and ADME studies DOI
S. N. Murthy Boddapati, Ramana Tamminana,

Hari Jyothi Senapathi

и другие.

Journal of Molecular Structure, Год журнала: 2025, Номер unknown, С. 141409 - 141409

Опубликована: Янв. 1, 2025

Язык: Английский

Процитировано

0
Synthesis of Primary and Secondary Amines via Electrochemical Reduction of Hydrazines DOI

Dong Wang,

Qiulu Wang,

Mingxia Liu

и другие.

Organic Letters, Год журнала: 2024, Номер 26(51), С. 11123 - 11128

Опубликована: Дек. 13, 2024

We herein introduce an electrochemical route for the N–N bond cleavage of hydrazines. This mild and green methodology utilized readily available mono- 1,1-disubstituted hydrazines or their HCl salts as starting materials to access a broad scope primary secondary amines in high yields. The mechanistic investigation suggests that amine product is formed by consecutive SET reduction, utilization hydrazine salt important providing sufficient conductivity acidity facilitate this reaction.

Язык: Английский

Процитировано

2
Triply Selective & Sequential Diversification at Csp3: Expansion of Alkyl Germane Reactivity for C−C & C−Heteroatom Bond Formation DOI Creative Commons

Eric Ahrweiler,

Markus D. Schoetz,

Gurdeep Singh

и другие.

Angewandte Chemie, Год журнала: 2024, Номер 136(16)

Опубликована: Фев. 22, 2024

Abstract We report the triply selective and sequential diversification of a single C sp 3 carbon carrying Cl, Bpin GeEt for modular programmable construction ‐rich molecules. Various functionalizations −Cl −BPin (e.g. alkylation, arylation, homologation, amination, hydroxylation) were tolerated by −GeEt group. Moreover, methodological repertoire alkyl germane functionalization was significantly expanded beyond hitherto known Giese addition arylation to alkynylation, alkenylation, cyanation, halogenation, azidation, C−S bond formation as well first demonstration stereo‐selective ‐[Ge] bond.

Язык: Английский

Процитировано

1
Recent Developments with Organogermanes: their Preparation and Application in Synthesis and Catalysis DOI Creative Commons
Tatiana Rogova,

Eric Ahrweiler,

Markus D. Schoetz

и другие.

Angewandte Chemie, Год журнала: 2023, Номер 136(8)

Опубликована: Окт. 30, 2023

Abstract Within the sphere of traditional Pd 0 /Pd II cross coupling reactions, organogermanes have been historically outperformed both in terms scope and reactivity by more conventional transmetalating reagents. Subsequently, this class compounds has largely underutilized as a partner bond‐forming strategies. Most recent studies, however, shown that alternative modes activation these notoriously robust building blocks transform into most reactive site molecule—capable outcompeting other functional groups (such boronic acids, esters silanes) for C−C C–heteroatom bond formation. As result, over past few years, literature increasingly featured methodologies explore potential chemoselective orthogonal partners. Herein we highlight some advances field organogermane chemistry with respect to their synthesis applications synthetic catalytic transformations.

Язык: Английский

Процитировано

1