Synthesis of indolines <i>via</i> a palladium/norbornene-catalyzed reaction of aziridines with aryl iodides

Liu, Ce; Liang, Yujie; Zheng, Nian; Zhang, Bo‐Sheng; Yuan, Fuqing; Bi, Siwei; Liang, Yong‐Min

doi:10.1039/c8cc01062e

Cited by 63 publications

(35 citation statements)

References 62 publications

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“…The most striking feature of this protocol is the excellent regio‐ and diastereoselectivity for 2‐alkyl and 2‐aryl‐substituted aziridines to access 1,3‐ cis ‐ and 1,4‐ cis ‐substituted tetrahydroisoquinolines 100 and 101 , respectively (Scheme ). Herein, the observed diastereoselectivity for 2‐alkyl‐substituted aziridines is different from that reported by Ferraccioli and co‐workers, whereas the observed regioselectivity for 2‐aryl‐substituted aziridines is different from that reported by the group of Liang …”

Section: H‐azirines and Aziridinescontrasting

confidence: 99%

“…Recently, Liang and co‐workers successfully employed N‐substituted aziridines as both the alkylating and terminating reagents for Catellani‐type reactions; thus developing a novel strategy to access various indolines through a direct annulation reaction between aryl iodide and readily available N‐sulfonated aziridines (Scheme ) . If simple 1‐tosylaziridine (R 5 =H) was reacted with various aryl iodides, the corresponding indoline products were obtained in yields of 16–87 %.…”

Section: H‐azirines and Aziridinesmentioning

confidence: 99%

“…[13] Recently,the groupsofLiang and Zhou independently identified aziridinesa sc ompetent alkylating reagents for reacting with aryl iodides fort he syntheses of indolines or tetrahydroisoquinolines through Pd/NBE cooperative catalysis. [14] Thus, the paradigm of alkylating regentsf or the Catellani reaction has been greatly expanded (Sections4and 5).…”

Section: Introductionmentioning

confidence: 99%

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Alkylating Reagents Employed in Catellani‐Type Reactions

Liu

Gao

Cheng

et al. 2018

Chemistry A European J

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The Catellani reaction is a powerful strategy that allows the expeditious synthesis of highly substituted arenes, which are not easily accessible through traditional transition-metal-catalyzed cross-coupling reactions. This reaction utilizes the synergistic interplay of palladium and norbornene catalysis to facilitate sequential ortho-C-H functionalization and ipso termination of aryl iodides in a single operation. Since pioneering work by the group of Catellani in 1997, and later by the group of Lautens, this chemistry has attracted considerable attention from the synthetic chemistry community. Dramatic progress has been made by a number of groups in the past two decades. In this Minireview, the alkylating reagents employed in this intriguing reaction and the corresponding applications in organic synthesis are summarized; thus complementing existing reviews to inspire future developments.

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Section: H‐azirines and Aziridinescontrasting

confidence: 99%

Section: H‐azirines and Aziridinesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Alkylating Reagents Employed in Catellani‐Type Reactions

Liu

Gao

Cheng

et al. 2018

Chemistry A European J

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“…The coordination geometry of Pd is distorted square‐planar with palladium coordinated to one phosphine, amide, aldehyde and norbornyl groups. The Pd‐C and Pd‐N distances [2.024(6) and 2.050(4) Å] are normal as compared with those of known Pd (II)‐alkyl [1.994(5)–2.053(3) Å] and Pd (II)‐amide [2.032(4)–2.055(2) Å] complexes . The C=O distance being 1.228(9) Å is relatively longer than free formyl groups [1.208(5)–1.211(5) Å],[10k] illustrating that oxygen is weakly coordinated.…”

Section: Resultsmentioning

confidence: 97%

Synthesis and characterization of palladium amido complexes containing pincer CNO ligands through nitrene insertion

Wang

Chen

2019

Applied Organom Chemis

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Catellani reactions of aryl iodides allow the double functionalization at the ortho and ipso positions in one pot. Catellani reactions involving a nitrene intermediate are not yet known. In this paper, a few palladium amino complexes were prepared from PdCl2, anthranil and iodoarenes, and their structures were determined by X‐ray single‐crystal diffraction. These complexes are supported by a pincer C,N,O tridentate ligand forming fused six‐membered palladacycles. The high stability of the palladium complexes inhibits their reductive elimination.

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“…An extension of the regular alkenes arylation according to the Heck coupling mechanism is the palladium-catalysed Heck–Catellani reaction, reported in 1985, which involves an intramolecular C-H bond activation and functionalisation [4]. This discovery provided the foundation for the majority of recent developments of direct C-H activation/C-C coupling reactions [5,6,7,8,9] that are conducted to improve the efficiency and atom economy of traditional couplings.…”

Section: Introductionmentioning

confidence: 99%

New Rigid Polycyclic Bis(phosphane) for Asymmetric Catalysis

et al. 2019

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A simple, highly efficient synthesis of a series of novel chiral non-racemic rigid tetracyclic phosphorus ligands, applicable in important chemical asymmetric transformations, was performed. In a tandem cross-coupling/C-H bond activation reaction, a well-recognised and readily available ligand (R,R)-NORPHOS was used as the starting material. The palladium complexes of new ligands were obtained and characterised on the example of a crystalline dichloropalladium complex of [(1R,2R,9S,10S,11R,12R)-4-phenyltetracyclo[8.2.1.02,9.03,8]trideca-3,5,7-triene-11,12-diyl]bis(diphenylphosphane). A notably high activity and stereoselectivity of the palladium catalysts based on the new ligands were confirmed in a model asymmetric allylic substitution reaction. Herein, we discuss the geometry of the palladium complexes formed and its impact on the efficiency of the catalysts. A comparison of their geometric features with other bis(phosphane) ligand complexes found in the Cambridge Structural Database and built density functional theory (DFT) commutated models is also presented and rationalised.

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Synthesis of indolines via a palladium/norbornene-catalyzed reaction of aziridines with aryl iodides

Cited by 63 publications

References 62 publications

Alkylating Reagents Employed in Catellani‐Type Reactions

Alkylating Reagents Employed in Catellani‐Type Reactions

Synthesis and characterization of palladium amido complexes containing pincer CNO ligands through nitrene insertion

New Rigid Polycyclic Bis(phosphane) for Asymmetric Catalysis

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