Synthesis of tetra-substituted olefins via annulation by Pd-catalyzed carbopalladation/C–H activation and solid state fluorescence properties

Naveen, Kanagaraj; Nandakumar, Avanashiappan; Perumal, Paramasivan T.

doi:10.1039/c5ra14621f

Cited by 6 publications

(2 citation statements)

References 60 publications

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“…We have already explored Rh(III)-catalyzed dehydrogenative C–H/N–H functionalization to synthesize cinnoline derivatives as fluorescent probes for live cancer cell imaging in our recent work. 13 In the course of our efforts on the development of novel transition metal-catalyzed C–H functionalization 14 and annulation reactions, 15 with the aim of design and synthesis of novel organic fluorophores, 16 we report here Ru(II)-catalyzed regiospecific C–H/O–H oxidative annulation reaction to synthesize isochromeno[8,1- ab ]phenazine, which was successfully applied as an FR fluorescent probe for live cancer cell imaging.…”

Section: Introductionmentioning

confidence: 99%

Ru(II)-Catalyzed Regiospecific C–H/O–H Oxidative Annulation to Access Isochromeno[8,1-ab]phenazines: Far-Red Fluorescence and Live Cancer Cell Imaging

et al. 2017

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A facile ruthenium(II)-catalyzed regiospecific C–H/O–H oxidative annulation methodology was developed to construct isochromeno[8,1-ab]phenazines. This methodology delivers various advantages, such as scope for diverse substrates, tolerance to a range of functional groups, stability under air, and yields regioselective products. This methodology was successfully applied to synthesize far red (FR) fluorescent probes for live cancer cell imaging. The synthesized compounds displayed notable fluorescence properties in solution and thin-film. Their application in live cancer cell imaging was investigated using various cancer cell lines. The synthesized compound showed prominent FR fluorescence, with high quantum yield, and exhibited better cell-imaging properties, with excellent biocompatibility.

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Section: Introductionmentioning

confidence: 99%

Ru(II)-Catalyzed Regiospecific C–H/O–H Oxidative Annulation to Access Isochromeno[8,1-ab]phenazines: Far-Red Fluorescence and Live Cancer Cell Imaging

et al. 2017

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“…In this context, Lautens et al developed an attractive domino approach based on the Catellani reaction to access sterically crowded olefins via a Pd-catalyzed multiple C–H activation . Consecutively, Tietze et al and Perumal et al realized the synthesis of multisubstituted olefins through Pd-catalyzed domino reactions . Although these methods have made a significant contribution to the synthesis of sterically hindered tetrasubstituted olefins, the development of a simple and step-economical domino approach for their efficient preparation is still highly desirable.…”

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confidence: 99%

Domino Palladium-Catalyzed Double Norbornene Insertion/Annulation Reaction: Expeditious Synthesis of Overcrowded Tetrasubstituted Olefins

2019

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A Pd-catalyzed domino process involving a double norbornene insertion/annulation reaction was developed for the expeditious synthesis of overcrowded olefins. In this one-pot reaction, four new C–C bond formations were achieved by three consecutive Heck carbopalladations and C–H activation across the CC triple bond of 2-alkynyl bromobenzenes with two norbornene rings via a reactive vinylic-Pd(II) species. This protocol provides a step-economical synthetic system to access the structurally identical molecular machine motifs of overcrowded olefins with high yields.

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Palladium‐Catalyzed Synthesis of Tetrasubstituted Olefins by Triple Domino Process

2017

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An efficient, highly regio-and stereoselective protocol for the synthesis of tetrasubstituted olefins was developed to take place by a palladium(0)-catalyzed triple domino process. It involves the formation of three new CÀC bonds through double carbopalladation and CÀH activation across 2-bromoaryl alkynyl biaryls/heteroaryls with norbornene. This method is practically simple with broad substrate scope and tolerates a wide range of substituents. The products bearing 9Hpyrrolo[1,2-a]indole motifs reveal intriguing solid state fluorescence properties and thus form a new class of aggregation induced emission (AIE) fluorophores.

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Synthesis of tetra-substituted olefins via annulation by Pd-catalyzed carbopalladation/C–H activation and solid state fluorescence properties

Cited by 6 publications

References 60 publications

Ru(II)-Catalyzed Regiospecific C–H/O–H Oxidative Annulation to Access Isochromeno[8,1-ab]phenazines: Far-Red Fluorescence and Live Cancer Cell Imaging

Ru(II)-Catalyzed Regiospecific C–H/O–H Oxidative Annulation to Access Isochromeno[8,1-ab]phenazines: Far-Red Fluorescence and Live Cancer Cell Imaging

Domino Palladium-Catalyzed Double Norbornene Insertion/Annulation Reaction: Expeditious Synthesis of Overcrowded Tetrasubstituted Olefins

Palladium‐Catalyzed Synthesis of Tetrasubstituted Olefins by Triple Domino Process

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