Palladium-Catalyzed C–H Alkenylation of Arenes Using Thioethers as Directing Groups

Yu, Ming; Xie, Yaowen; Xie, Changde; Zhang, Yuhong

doi:10.1021/ol3006997

Cited by 163 publications

(59 citation statements)

References 59 publications

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“…To the best of our knowledge, just one example of ringopening/ring-closing process of the rhodanine core is reported in the literature. [12] Differently from this, our sequence occurs with the loss of a molecule of carbon disulfide, which activates the substituted nitrogen atom of the rhodanine as nucleophile in the first cyclization event.…”

Section: Resultsmentioning

confidence: 96%

Unexpected Synthesis of 2,3,5,6‐Tetrahydro‐1H‐pyrrolo[3,4‐c]pyridine‐1,3,6‐triones by a Double Michael Addition/CS₂ Extrusion/Double Cyclization Sequence

et al. 2017

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Bis adducts derived from a double Michael addition of rhodanine to an azo‐ene system of two molecules of 1,2‐diaza‐1,3‐dienes (DDs) have furnished the corresponding 2,3,5,6‐tetrahydro‐1H‐pyrrolo[3,4‐c]pyridine‐1,3,6‐triones by means of a CS2 extrusion/double cyclization sequence. The incorporation of two units (4 and 2 atoms) of DDs into the fused bicyclic heterocycles represents a new application of this versatile class of molecules in heterocyclic synthesis.

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Section: Resultsmentioning

confidence: 96%

Unexpected Synthesis of 2,3,5,6‐Tetrahydro‐1H‐pyrrolo[3,4‐c]pyridine‐1,3,6‐triones by a Double Michael Addition/CS₂ Extrusion/Double Cyclization Sequence

et al. 2017

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“…[68] Another method, involving copper ion mediated rhodamine spirolactam ring opening was developed by Xiao and co-workers (Scheme 39). [69] Conversion of the regioisomeric mixtures to their corresponding hydrazide in isomerically pure form was achieved by treatment with hydrazine hydrate followed by column purification of the respective formed hydrazide. Further, a copper(II) chloride mediated hydrolysis then yielded the 5th regioisomer in moderate yield (approx.…”

Section: Improved Synthesis Of 9-arylxanthene Based Dyesmentioning

confidence: 99%

Conformationally Restricted Triarylmethanes: Synthesis, Photophysical Studies, and Applications

2018

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Triarylmethanes, compounds in which the central carbon atom is attached to three aryl rings, have a wide variety of photophysical properties which are utilized in the dye industry and also in the development of novel fluorescent tags and biomarkers. The aryl rings attached to the central carbon atom of the parent molecule triphenylmethane can freely rotate. Bridging the aryl rings of triarylmethanes with heteroatoms or through bonds decreases the conformational flexibility enjoyed by the parent molecules. Conformationally restricted triarylmethane (CRT) molecules like 9‐arylxanthenes (oxygen bridging), 9‐arythioxanthenes (sulfur bridging), 9,10‐dihydro,9‐arylacridines (nitrogen bridging), and 9‐arylfluorenes (bridging through C–C bond) have decreased conformational flexibility and display amphihydric behavior which results in benzenoid structure and quinoid structure of these molecules. The quinoid form of these molecules displays very rich photophysical properties which are the subject of this review. These molecules also have widespread utility, and over the last decade, a number of studies have been focused on the synthesis, photophysical properties, and applications of molecules derived from this core structure. Through this review, we intend to give the readers an outlook on the different strategies employed to synthesize these molecules and also provide a broader perspective on the various intriguing properties of these molecules. The applications of these classes of molecules in diverse fields like photocatalysis, chemical biology, pharmaceutical chemistry, and bio‐imaging are discussed. Also, the areas that need to be further developed are highlighted, which may provide a further impetus in the development of this class of molecules.

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“…[10] However,several drawbacks, including low selectivity,has limited the practicality of this transformation. This drawback is miti-gated by chelation-assisted CÀHf unctionalization strategies in which ad iverse range of directing groups including ureas, [11] thioethers, [12] anilides, [13] amides, [14] hydrazones, [15] 1,2,3-triazoles, [16] carboxylic acids, [17] and carbamates, [18] have been reported.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Benzopyrans by Enolate‐Directed Rhodium‐Catalyzed Oxidative C−H Alkenylation of 1,3‐Dicarbonyl Compounds

et al. 2017

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Ad iverses cope of 2-aryl-1,3-dicarbonyl substrates was investigated in an efficient and facile enolate-directed CÀHa lkenylation process using readily availablee lectron-deficient alkenes. The developed domino strategy works under rhodium catalysis, providing ar ange of benzopyran heterocycles by the formationo ft wo distinct CÀCa nd CÀOb onds and one new six-membered ring. The salient features of the protocoli nclude the broad range of previously unexplored 1,3-dicarbonyl substrates for CÀHa lkenylations, good functional group tolerance and rapid assembly of new benzopyrans in generally good to excellent isolated yields. Figure 1. Selected examples of bioactive benzopyrans.[a] Dr.

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Palladium-Catalyzed C–H Alkenylation of Arenes Using Thioethers as Directing Groups

Cited by 163 publications

References 59 publications

Unexpected Synthesis of 2,3,5,6‐Tetrahydro‐1H‐pyrrolo[3,4‐c]pyridine‐1,3,6‐triones by a Double Michael Addition/CS₂ Extrusion/Double Cyclization Sequence

Unexpected Synthesis of 2,3,5,6‐Tetrahydro‐1H‐pyrrolo[3,4‐c]pyridine‐1,3,6‐triones by a Double Michael Addition/CS₂ Extrusion/Double Cyclization Sequence

Conformationally Restricted Triarylmethanes: Synthesis, Photophysical Studies, and Applications

Synthesis of Benzopyrans by Enolate‐Directed Rhodium‐Catalyzed Oxidative C−H Alkenylation of 1,3‐Dicarbonyl Compounds

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Palladium-Catalyzed C–H Alkenylation of Arenes Using Thioethers as Directing Groups

Cited by 163 publications

References 59 publications

Unexpected Synthesis of 2,3,5,6‐Tetrahydro‐1H‐pyrrolo[3,4‐c]pyridine‐1,3,6‐triones by a Double Michael Addition/CS2 Extrusion/Double Cyclization Sequence

Unexpected Synthesis of 2,3,5,6‐Tetrahydro‐1H‐pyrrolo[3,4‐c]pyridine‐1,3,6‐triones by a Double Michael Addition/CS2 Extrusion/Double Cyclization Sequence

Conformationally Restricted Triarylmethanes: Synthesis, Photophysical Studies, and Applications

Synthesis of Benzopyrans by Enolate‐Directed Rhodium‐Catalyzed Oxidative C−H Alkenylation of 1,3‐Dicarbonyl Compounds

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Product

Resources

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Unexpected Synthesis of 2,3,5,6‐Tetrahydro‐1H‐pyrrolo[3,4‐c]pyridine‐1,3,6‐triones by a Double Michael Addition/CS₂ Extrusion/Double Cyclization Sequence

Unexpected Synthesis of 2,3,5,6‐Tetrahydro‐1H‐pyrrolo[3,4‐c]pyridine‐1,3,6‐triones by a Double Michael Addition/CS₂ Extrusion/Double Cyclization Sequence