Cited by Rh-Catalyzed Functionalization of N-Heterocycles Through C

Rh-Catalyzed [3+2] Annulation of Cyclic Ketimines and Alkynyl Chloride: A Strategy for Accessing Unsymmetrically Substituted and Highly Functionalizable Indenes DOI

Xu Zhao,

Chenrui Fan,

Jianbo He

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(50), P. 9169 - 9173

Published: Dec. 12, 2022

Alkynyl chlorides were found to be extraordinarily novel electrophiles, which could afford a single regioisomer of the [3+2] annulation adducts with cyclic ketimines by rhodium catalysis. The alkenyl chloride moiety in products provided valuable functional handle for further diverse transformations. Therefore, this research not only synthetic protocol accessing unsymmetrically substituted indenyl amines but also highly divergent solution decorating substituting group postmanipulation chloride.

Language: Английский

Citations

Cp*Co(III)-Catalyzed C–H Hydroarylation of Alkynes and Alkenes and Beyond: A Versatile Synthetic Tool DOI

Asier Carral‐Menoyo, Nuria Sotomayor, Esther Lete

et al.

ACS Omega, Journal Year: 2020, Volume and Issue: 5(39), P. 24974 - 24993

Published: Sept. 15, 2020

The use of earth-abundant first-row transition metals, such as cobalt, in C–H activation reactions for the construction and functionalization a wide variety structures has become central topic synthetic chemistry over last few years. In this context, emergence cobalt catalysts bearing pentamethylcyclopentadienyl ligands (Cp*) had major impact on development methodologies. Cp*Co(III) complexes have been proven to possess unique reactivity compared, example, their Rh(III) counterparts, obtaining improved chemo- or regioselectivities, well yielding new reactivities. This perspective is focused recent advances alkylation alkenylation (hetero)arenes with alkenes alkynes under catalysis.

Language: Английский

Citations

Recent Advances in the Synthesis of 5‐MemberedN‐Heterocycles via Rhodium Catalysed Cascade Reactions DOI

Deepak Ranjan Mishra, Bhabani Shankar Panda, Sabita Nayak

et al.

ChemistrySelect, Journal Year: 2022, Volume and Issue: 7(22)

Published: June 9, 2022

Abstract Five membered N ‐heterocycles are significant targets in organic synthesis because of their ubiquitous existence bioactive natural products and pharmaceuticals. Over the past decade a compelling attractiveness has grown to develop rhodium complex catalysed efficient atom‐economic chemistry access structurally diverse ‐heterocyclic frameworks. This present review enlightens notable progresses advances 5‐membered via cascade reactions (annulations, C−H/C−C activation, cycloaddition, rearrangement, cyclization, metathesis) from 2018–2021.

Language: Английский

Citations

Modern metal-catalyzed and organocatalytic methods for synthesis of coumarin derivatives: a review DOI

Sara Moghadam Farid,

Behnoush Seifinoferest,

Maral Gholamhosseyni

et al.

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(24), P. 4846 - 4883

Published: Jan. 1, 2022

Coumarin is an important pharmaceutical structural motif, abundantly found in numerous commonly used drugs. Compounds containing this core show a broad spectrum of medicinal properties and biological activities. The increasing importance wide usages coumarin derivatives have drawn attention to its synthetic methods, among which metal-catalyzed organocatalytic methods proved the most effective. Several and/or strategies for been investigated reported recent decades. This review focuses on more reports catalysis synthesizing coumarin-like structures (including light-mediated nano-catalysts), exploring mechanistic aspects, simplicity, efficiency, repeatability, other advantages disadvantages these methods.

Language: Английский

Citations

Asymmetric [5+1] Annulation via C–H Activation/1,4-Rh Migration/Double Bond Shift Using a Transformable Pyridazine Directing Group DOI

Man Zhu,

Yuyao Zhao,

Xingwei Li

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(11), P. 1839 - 1844

Published: March 13, 2023

N-Heterocycle-assisted C-H activation/annulation reactions have provided new concepts for the construction and transformation of azacycles. In this work, we disclose a [5+1] annulation reaction using novel transformable pyridazine directing group (DG). The DG-transformable mode led to heterocyclic ring accompanied by original via activation/1,4-Rh migration/double bond shift pathway, affording skeleton pyridazino[6,1-b]quinazolines with good substrate scope under mild conditions. Diverse fused cyclic compounds can be achieved derivatization product. asymmetric synthesis was also realized afford enantiomeric products stereoselectivity.

Language: Английский

Citations

Photocatalytic [2+2+m] Cyclization of 2‐Cyanoaryl Acrylamides with 2‐Bromocarbonyls Involving C(sp³)−H Functionalization DOI

Chuan Liu,

Guangpeng Yan,

Zonglang Wu

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(24), P. 4513 - 4519

Published: Oct. 31, 2023

Abstract An oxidant‐free photocatalytic [2+2+m] cyclization of 2‐cyanoaryl acrylamides with 2‐bromocarbonyls is reported, enabling the assembly biologically important N‐heterocycle‐fused quinolinones including benzo[1,6]naphthyridinones and pyrrolo[3,2‐ c ]‐quinolines. This protocol proceeds through a radical relay pathway alkene difunctionalization along an intramolecular cyano insertion subsequent site‐specific functionalization inert C( sp 3 )−H bond enabled by cyano‐derived iminyl radical‐mediated 1,n‐hydrogen atom transfer. Notably, this transformation selectively formed two distinct C−C bonds, one C−N bond, quaternary carbon center in one‐pot procedure.

Language: Английский

Citations

Palladium iodide catalyzed carbonylative double cyclization to a new class of S,O-bicyclic heterocycles DOI

Raffaella Mancuso, Patrizio Russo,

Rossana Miliè

et al.

Catalysis Today, Journal Year: 2021, Volume and Issue: 397-399, P. 631 - 638

Published: May 19, 2021

Language: Английский

Citations

Rhodium-catalyzed annulation for the construction of indole core: An update DOI

Suven Das, Arpita Dutta

Tetrahedron, Journal Year: 2023, Volume and Issue: 146, P. 133633 - 133633

Published: Sept. 11, 2023

Language: Английский

Citations

1,3,5‐Triaza‐7‐phosphaadamantane (PTA) Derived Caged Phosphines for Palladium‐Catalyzed Selective Functionalization of Nucleosides and Heteroarenes DOI

Siva Sankar Murthy Bandaru,

Shatrughn Bhilare, Carola Schulzke

et al.

The Chemical Record, Journal Year: 2020, Volume and Issue: 21(1), P. 188 - 203

Published: Nov. 24, 2020

Abstract Phosphines have, in combination with transition metals, played a pivotal role the rapid development of efficient catalytic processes. Caged phosphines constitute class three‐dimensional scaffolds providing unique control over steric and electronic properties. The versatility caged phosphine ligands has been demonstrated elegantly by groups Verkade, Gonzalvi as well Stradiotto. Our research group also working extensively for past several years 1,3,5‐triaza‐7‐phosphaadamantane‐based this personal note we have summarized these applications pertaining to modification biologically useful nucleosides heteroarenes.

Language: Английский

Citations

Rhodium-Catalyzed Redox-Neutral Olefination of Aryldiazenes with Acrylate Esters via C–H Activation and Transfer Hydrogenation DOI

Xiaofei Zhang, Bin Zhang, Xingwei Li

et al.

Organic Letters, Journal Year: 2021, Volume and Issue: 23(5), P. 1687 - 1691

Published: Feb. 16, 2021

Rh(III)-catalyzed redox-neutral C–H olefination of aryldiazenecarboxylates has been realized using arylate esters as the olefinating reagents. This reaction proceeds under mild and conditions, resulting in integration activation transfer hydrogenation. The chemoselectivity complements that previously reported rhodium-catalyzed coupling same substrates.

Language: Английский

Citations