Through‐Space 1,4‐Palladium Migration and 1,2‐Aryl Shift: Direct Access to Dibenzo[<i>a</i>,<i>c</i>]carbazoles through a Triple CH Functionalization Cascade

Bhunia, Samir Kumar; Polley, Arghya; Natarajan, Ramalingam; Jana, Ranjan

doi:10.1002/chem.201503474

Cited by 76 publications

(28 citation statements)

References 84 publications

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“…Alternatively, a 1,2‐Pd shift of M7 gave tertiary palladium species M9 , which favored the 1,2‐aryl shift to provide M10 . Subsequent deprotonation and intramolecular arylation formed compound 29 …”

Section: 4‐palladium Migration Reactionsmentioning

confidence: 99%

1,4‐Migration of Transition Metals in Organic Synthesis

Rahim

Feng

2019

Chin. J. Chem.

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Generation of carbon‐metal species is extremely important in transition metal‐catalyzed organic synthesis. Among the various methods, 1,4‐metal migration is a very useful way to create new carbon‐metal species, which are not readily accessible via classic methods. This review summarized recent advances in transition metal‐catalyzed reactions, which involved one or more steps of 1,4‐metal migration. It focused mostly on the achievements in Pd and Rh‐catalyzed reactions, along with some of the remarkable results in Pt, Ir, Co, Fe‐involved transformations.

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Section: 4‐palladium Migration Reactionsmentioning

confidence: 99%

1,4‐Migration of Transition Metals in Organic Synthesis

Rahim

Feng

2019

Chin. J. Chem.

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“…132 The authors applied cascade reaction to diversely substituted 2-aryl indoles (Scheme 100, top). 132 Interestingly, the reaction tolerated halogen substituents such as bromo, chloro, and fluoro, which could be useful for further transformations to extend the π-system. Only non or para-substituted diaryliodonium salts have been employed.…”

Section: Annulation Through Pd-catalyzed C-h Bond Arylationmentioning

confidence: 99%

Application of Palladium-Catalyzed C(sp2)–H Bond Arylation to the Synthesis of Polycyclic (Hetero)Aromatics

Hagui

Doucet

2019

Chem

123

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Recently, the use of the palladium-catalyzed inter-and/or intra-molecular C-H bond arylations in the building of various π-extended (hetero)aromatic structures has emerged as a suitable alternative to the previous multi-steps synthesis. Such new methodology even allowed to prepare unprecedented π-extended molecules owing a perfect control of the reaction sites. This review gives an overview of various synthesis of Polycyclic Aromatic Hydrocarbons (PAHs) and PolyCyclic Heteroaromatics (PCHs) with planar, bowl-shaped, and helical structures prepared in high efficiency and selectivity via Pd-catalyzed C-H bond arylations. Bigger Picture Recently, π-extended compounds such as Polycyclic Aromatic Hydrocarbons (PAHs) and PolyCyclic Heteroaromatics (PCHs) have found important applications in the preparation of optoelectronic devices. The degree of π-extension, the topology of the ring fusion, and the periphery of such molecules are essential factors to control their electronic properties at a molecular level. The traditional approach to prepare nanographenes and heteroatom-doped nanographenes relies on Scholl reaction. However, such methodology suffers from limitations such as functional group compatibility. Catalysis plays a pivotal role in the discovery of new transformations enabling the synthesis of novel molecules, including organic materials. Among various catalytic transformations, Pd-catalyzed C-H bond arylation has emerged as an important tool for the construction of well-decorated polycyclic (hetero)aromatic molecules. Such direct approaches have a considerable impact on the synthesis of PAHs and PCHs by shortening the synthetic scheme and also providing a momentous opportunity to design novel structures. eTOC Blurb: This review highlights the potential of Pd-catalyzed C-H bond arylation for the synthesis of π-extended compounds that include

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“…Due to variable valence as well as selective reactivity of hypervalent iodine compounds have been extensively explored for the site‐selective C−H activation. In 2015, Jana and co‐workers [31] reported a palladium‐catalyzed one‐step synthesis of dibenzofused carbazoles employing three C−C bond formation from 2‐arylated indoles (Scheme 23).…”

Section: Metal‐catalyzed Aryl‐aryl Cross‐coupling Reactions Using Hypmentioning

confidence: 99%

Aryl‐Aryl Cross‐Coupling with Hypervalent Iodine Reagents: Aryl Group Transfer Reactions

Ghosh

Rout

2020

ChemistrySelect

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Aryl-aryl cross-coupling are a unique class of CÀ C bond formation reaction in organic chemistry. From last few years, various synthetic methods have been developed for aryl-aryl cross-coupling reaction using hypervalent iodine (III) reagents as an aryl group donor. This review highlights exciting synthetic protocols that have been used for aryl-aryl cross-coupling reactions with hypervalent iodine reagents employing aryl group transfer reaction. The review has categorized the metal-catalyzed and metal free aryl-aryl cross-coupling reactions separately using hypervalent iodine reagents. Also this review provides the mechanistic prospective involves for arylgroup transfer reaction.

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Through‐Space 1,4‐Palladium Migration and 1,2‐Aryl Shift: Direct Access to Dibenzo[a,c]carbazoles through a Triple CH Functionalization Cascade

Cited by 76 publications

References 84 publications

1,4‐Migration of Transition Metals in Organic Synthesis

1,4‐Migration of Transition Metals in Organic Synthesis

Application of Palladium-Catalyzed C(sp2)–H Bond Arylation to the Synthesis of Polycyclic (Hetero)Aromatics

Aryl‐Aryl Cross‐Coupling with Hypervalent Iodine Reagents: Aryl Group Transfer Reactions

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