Fe‐Catalyzed Aliphatic C−H Methylation of Glycine Derivatives and Peptides DOI

Silin Song,

Xiuliang Cheng,

Shiyan Cheng

et al.

Chemistry - A European Journal, Journal Year: 2022, Volume and Issue: 29(17)

Published: Dec. 22, 2022

Direct and selective C-H methylation is a powerful tool with which to install methyl groups into organic molecules, particularly useful in pharmaceutical chemistry. However, practical methods for such modification of biologically interesting targets have been rarely developed. We here report an iron-catalyzed C(sp3 )-H reaction glycine derivatives, peptides drug-like molecules alcohol the presence di-tert-butyl peroxide. A readily available iron catalyst plays multiple roles transformation, accelerates oxidation C-N bonds C=N double bonds, activates imine intermediates as Lewis acids by bidentate chelation, at same time facilitates cleavage peroxide generate radicals. variety methylated N-aryl derivatives were obtained good yield excellent chemo- site-selectivity. This scalable, easily managed, can be completed within 1-2 h. It features economic, bio-friendly catalyst, green solvent low toxic reagents, will provide effective access precise biomolecules natural products.

Language: Английский

Visible-Light-Induced Annulation of Iodonium Ylides and 2-Isocyanobiaryls to Access 6-Arylated Phenanthridines DOI
Jinyang Chen, Hongyu Wu,

Hai‐Yang Song

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(13), P. 8360 - 8368

Published: June 1, 2023

A 1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene (4-CzIPN)-photocatalyzed cascade arylation/cyclization reaction of 2-isocyanobiaryls and iodonium ylides was established for the synthesis 6-arylated phenanthridines. This is first example employing as aryl radical sources in a visible-light-induced cyclization reaction.

Language: Английский

Citations

13
The Pyridotriazole Works as a Traceless Directing Group: A C–H Activation/Annulation Cascade Reaction with Iodonium Ylides DOI

Guanghui Lv,

Qingyao Zhang,

Cuimei Zhang

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(22), P. 4022 - 4027

Published: May 26, 2023

A novel Rh-catalyzed cascade reaction of pyridotriazoles with iodonium ylides is reported. This one-pot procedure involves a triazole-directed ortho-position C–H carbene insertion, followed by intramolecular denitrogenation annulation. It was noteworthy that this provided straightforward access to 1H-isochromene frameworks excellent yields (up 94% yield).

Language: Английский

Citations

12
Rh(III)-Catalyzed C–H Annulation of N-Nitrosoanilines with Iodonium Ylides for the Synthesis of N-Alkyl Indoles DOI

Chaoshui Liu,

Qiuzi Dai,

Yaqian Li

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(11), P. 7281 - 7289

Published: May 19, 2023

A novel protocol for synthesizing N-alkyl indoles from readily available N-nitrosoanilines and iodonium ylides through the rhodium(III)-catalyzed C-H bond activation/intramolecular cyclization reaction has been described. This strategy employs nitroso as a traceless directing group. The transformation features powerful reactivity, tolerates various functional groups, proceeds with moderate yields under mild conditions, providing straightforward approach to access structurally diverse valuable indole derivatives.

Language: Английский

Citations

11
Synthesis of 1-Aminoisoquinolines via Rh(III)-Catalyzed C–H Cascade Annulation of Benzamidines with Iodonium Ylides DOI
He Li, Bin Wu, Tao Chen

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: March 10, 2025

A Rh(III)-catalyzed C-H cascade annulation reaction of benzamidine hydrochlorides with iodonium ylides has been successfully accomplished, providing an efficient strategy for the synthesis various 1-aminoisoquinoline derivatives in moderate to good yields. Here, ylide serves as accessible and safe carbene precursor. Further derivatizations were implemented demonstrate potential utility this reaction. Furthermore, photophysical properties these compounds may have applications photoelectric materials.

Language: Английский

Citations

0
Ru(II)-Catalyzed C–H Functionalization of 2-Arylbenzimidazoles with Iodonium Ylides: A Straightforward Access to Bridgehead Polycyclic N-Heterocycles DOI
Saiprasad Nunewar, Sanjeev Kumar,

Akhilesh Waman Meshram

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(21), P. 13757 - 13762

Published: Oct. 25, 2022

Herein, we disclose an efficient ruthenium-catalyzed C–H functionalization of 2-arylbenzimidazoles/2-arylimidazoles with iodonium ylides leading to substituted tetracyclic and pentacyclic bridgehead N-heterocycles, wherein ylide acts as a carbene precursor. For the first time, proceeds through Ru–carbenoid intermediate. Further, synthetic utility this protocol was successfully shown for gram-scale synthesis useful transformations.

Language: Английский

Citations

18
Regioselective [3+2]‐Spiroannulation and [4+n]‐Annulation Approaches through Activation of C−H Bond Facilitated by Ru(II) as Catalyst: Role of Solvent Selectivity DOI
Rahul Dev Mandal, Anindita Sarkar, Dwaipayan Das

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(8), P. 1863 - 1876

Published: Feb. 21, 2024

Abstract Ru(II)‐catalyzed and solvent‐switched [3+2]‐spiroannulation [4+n] (n=1, 2, 3) annulations of 2‐aryl quinazolinone or 2‐aryl‐2,3‐dihydrophthalazine‐1,4‐diones with ynones alkynyl alcohol 1,3‐diynes under mild reaction conditions have been analyzed. These reactions take place in the presence appropriate solvent features a redox‐neutral pathway. Ynone serves as an ‘atypical one‐carbon unit’ [4+1] annulation generates tetrasubstituted carbon center bearing diverse heterocycles through [3+2] strategies. Post transformations synthesized spiro‐products augments potential developed methodology.

Language: Английский

Citations

3
Solvent‐Dependent Divergent Cyclization of Bicyclo[1.1.0]butanes DOI Creative Commons
Fuhao Zhang, Subhabrata Dutta, Alessia Petti

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 17, 2024

Bicyclo[1.1.0]butanes (BCBs) have recently garnered significant research interest as versatile precursors for synthesizing potential [n.1.1] bioisosteres and multi-functionalized cyclobutanes in a straightforward atom-economical manner. Here, we report solvent-dependent divergent cyclization of BCBs that provides highly diastereospecific decorated oxygen-containing bicyclo[3.1.1]heptanes (BCHeps), which serve meta-substituted arenes. Additionally, an unprecedented 1,2-difunctionalization reaction mode was explored, thus expanding the chemical space arene functionalized cyclobutanes.

Language: Английский

Citations

3
Visible-Light-Mediated Solvent-Switched Photosensitizer-Free Synthesis of Polyfunctionalized Quinolines and Pyridines DOI
Hirendra Nath Dhara, Amitava Rakshit, Tipu Alam

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(3), P. 471 - 476

Published: Jan. 13, 2023

A solvent (2,2,2-trifluoroethanol (TFE) vs ethyl alcohol (EtOH)) switched synthesis of quinolines and pyridines is illustrated from (E)-2-(1,3-diphenylallylidene)malononitriles via a Pd(II)-catalyzed photochemical process. The active catalyst [L2Pd(0)] generated serves as an exogenous photosensitizer. process offers predominantly Z-alkenylated in TFE EtOH, respectively. Furthermore, large-scale few interesting post-synthetic modifications have been demonstrated.

Language: Английский

Citations

8
Rhodium(III)-Catalyzed C–H Activation/[5 + 2] Cascade Annulation of Aroyl Hydrazides with Iodonium Ylides for the Synthesis of Seven-Membered Dibenzodiazepinediones DOI
He Li, Tao Chen,

Zhiwei Wang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Aug. 30, 2024

A novel Rh(III)-catalyzed C-H activation/[5 + 2] cascade annulation of aroyl hydrazides with iodonium ylides is accomplished, in which diverse seven-membered dibenzodiazepinediones were afforded moderate to excellent yields. This reaction features an ideal functional group tolerance and a wide substrate scope. Large-scale derivatization reactions conducted demonstrate the potential utility this transformation.

Language: Английский

Citations

2
1,3‐Diynes: A Versatile Precursor in Transition‐Metal Catalyzed (Mediated) C−H Functionalizations DOI
Sanjeev Kumar,

Tharun Kumar Sabbi,

Rasika Pingale

et al.

The Chemical Record, Journal Year: 2022, Volume and Issue: 23(3)

Published: Dec. 13, 2022

Abstract Transition metal‐catalyzed C−H functionalization of diverse arenes with alkyne units has attracted enormous attention for decades since they provide straightforward access to various functionalization/annulations, which are commonly present in bioactive compounds and natural products. Recently, conjugated alkynes (1,3‐diynes) have been utilized as key coupling partner many activation reactions due their versatile characteristic properties. The presence two C≡C bonds 1,3‐diyne brings the new diversity synthetic transformations, such chemo‐, regioselective pathways, mono‐bis functionalizations, cascade annulations, etc. Herein, we summarized latest developments realm transition‐metal‐catalyzed functionalizations 1,3‐diynes. Moreover, highlighted conditions, mechanisms applications corresponding reaction detail.

Language: Английский

Citations

9