Palladium/Norbornene‐Catalyzed Synthesis of Heteroatom‐Containing <i>o</i>‐Teraryls from Aryl Iodides and Heteroarenes through Double CH Activation in Sequence

Cà, Nicola Della; Maestri, Giovanni; Catellani, Marta

doi:10.1002/chem.200900843

Cited by 56 publications

(14 citation statements)

References 82 publications

(69 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…More recently norbornene/Pd-catalyzed sequences involving the ortho-arylation/ C-H arylation of heteroarenes have been introduced [54]. Heteroaryl substrates such as furan, thiophene, and pyrroles could be employed successfully, allowing an expeditious synthesis of heteroatom-containing o-teraryl derivatives such as 59 ( Fig.…”

Section: Aromatic Arylations Coupled With C-h Activationsmentioning

confidence: 99%

Bibliographical Background: The Ortho Effect in The Catellani Reaction

Larraufie

2013

Development of New Radical Cascades and Multi-Component Reactions

View full text Add to dashboard Cite

Pallado-catalyzed sequential reactions involving direct C-H bond activations have emerged as powerful tools for rapid access to complex polycyclic scaffolds, starting from simple precursors [1][2][3]. In this context, Professor Marta Catellani has pioneered in the mid 1980s the utilization of norbornene in cooperation with palladium to achieve sequential C-halide and C-H activations via the formation of a five-membered alkylaromatic palladacycle. In 1985, she published the synthesis of dihydrophenanthrene 1 by coupling of two molecules of bromobenzene and one of norbornene, through the proposed formation of palladacycle 2 ( Fig. 7.1) [4].Since then, numerous applications of palladium/norbornene-mediated domino processes have been reported, allowing the synthesis of various polycyclic frameworks and the construction of up to three carbon-carbon bonds in a single reaction [5][6][7]. The catalytic cycle of the Catellani reaction, involving multiple oxidation state of palladium (0, II and potentially IV), will be presented first. Several examples of the synthetic scope of this methodology will follow, with a special focus on the sequences involving aryl-aryl coupling. Palladacycle FormationThe Catellani reaction is based on the formation of palladium(II) metallacycles 7 and their ability to react with electrophiles such as aryl and alkyl halides. The palladacycle is generated from palladium(0) complex 3, aryl halide 4 and norbornene. Generally, Pd(0) catalysts are not air stable, so the in situ generation of Pd(0) species by reaction of palladium(II) salts with phosphines [8,9]

show abstract

Section: Aromatic Arylations Coupled With C-h Activationsmentioning

confidence: 99%

Bibliographical Background: The Ortho Effect in The Catellani Reaction

Larraufie

2013

Development of New Radical Cascades and Multi-Component Reactions

View full text Add to dashboard Cite

show abstract

“…Again in 2009, Catellani and co‐workers described the synthesis of the thiophene‐containing ortho ‐teraryl 108 by a one‐pot Pd(OAc) 2 /norbornene‐catalyzed reaction of 1‐iodo‐2‐isopropylbenzene with a large molar excess of thiophene ( 107 ) (Scheme ) 80…”

Section: Intermolecular Direct (Hetero)arylation Of Five‐membered Hmentioning

confidence: 99%

“…The reaction was also extended to the case involving 3,4‐ethylenedioxythiophene ( 109 ), an ortho ‐substituted aryl iodide and an ortho ‐substituted aryl bromide instead of two molecules of an ortho‐ substituted aryl iodide. Compound 110 was so prepared in 49% yield (Scheme ) 80,81…”

Section: Intermolecular Direct (Hetero)arylation Of Five‐membered Hmentioning

confidence: 99%

Nachrichten des Verbandes Biologie, Biowissenschaften & Biomedizin in Deutschland

2015

Biologie in unserer Zeit

View full text Add to dashboard Cite

show abstract

“…Catellani [61] reported a palladium/norbornene-catalyzed synthesis of heteroatom-containing o-teraryls from aryl iodides and heteroarenes (including indoles and pyrroles) through double C-H arylation. Fagnou's group [62] applied their own protocol (Pd(II)/Ag(I)/carboxylic acid) to achieve the direct arylation of azaindoles.…”

Section: Indoles and Pyrroles -Electron-rich Heteroarenesmentioning

confidence: 99%