Synthesis of a novel bridged 2-(cyclopentadienyl)-indene system using Pd-catalyzed Negishi-type cross coupling

Tews, D.; Gaede, Petra Escarpa

doi:10.1016/j.tetlet.2004.10.042

Cited by 9 publications

(7 citation statements)

References 13 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[139b] In another protocol, aN egishi-type cross-coupling reaction was successfully employed for the synthesis of 2-(4-tert-butylcyclopenta-1,4-dienyl)-1H-indene 374 startingf rom 2-bromo-1H-indene 372 and LiCptBu 373,c arriedo ut in the presence of [Pd(dppf)Cl 2 ]·CH 2 Cl 2 and ZnCl 2 (Scheme 144). [140] AP d-catalyzed alkoxycarbonylation, starting from 2-bromoindenones 375 and leadingt o1 -oxo-3-phenyl-1H-indene-2-carboxylates 376,w as also reported recently (Scheme 145). [141] Indenyllithiumd erivatives, readily availableb yl ithiation of indenes,a re useful nucleophilic precursors for the preparation of substituted indenes by reactionw ith suitable electrophiles.…”

Section: Functionalizationo Fc Yclic Precursorssupporting

confidence: 68%

“… Synthesis of 2‐(4‐ tert ‐butylcyclopenta‐1,4‐dienyl)‐1 H ‐indene 374 by Negishi‐type cross‐coupling between 2‐bromo‐1 H ‐indene 372 and LiCp t Bu 373 …”

Section: Synthesis Of Indenesmentioning

confidence: 99%

“…Synthesis of 2-(4-tert-butylcyclopenta-1,4-dienyl)-1H-indene 374 by Negishi-typec ross-coupling between 2-bromo-1H-indene 372 and LiCptBu 373. [140] Scheme145. Synthesis of 1-oxo-3-phenyl-1H-indene-2-carboxylates 376 by Pd-catalyzeda lkoxycarbonylation of 2-bromoindenones 375.…”

Section: Functionalizationo Fc Yclic Precursorsmentioning

confidence: 99%

“…For example, the Suzuki–Miyaura, Negishi, and Murahashi couplings, carried out with 4‐ or 7‐halo‐1 H ‐indenes as substrates, afforded the corresponding arylindenes in moderate to high yields, as exemplified in Scheme for the conversion of 7‐bromo‐1 H ‐indene 370 into 7‐phenyl‐1 H ‐indene 371 . In another protocol, a Negishi‐type cross‐coupling reaction was successfully employed for the synthesis of 2‐(4‐ tert ‐butylcyclopenta‐1,4‐dienyl)‐1 H ‐indene 374 starting from 2‐bromo‐1 H ‐indene 372 and LiCp t Bu 373 , carried out in the presence of [Pd(dppf)Cl 2 ]⋅CH 2 Cl 2 and ZnCl 2 (Scheme ) . A Pd‐catalyzed alkoxycarbonylation, starting from 2‐bromoindenones 375 and leading to 1‐oxo‐3‐phenyl‐1 H ‐indene‐2‐carboxylates 376 , was also reported recently (Scheme ) …”

Section: Synthesis Of Indenesmentioning

confidence: 99%

See 3 more Smart Citations

Recent Advances in the Synthesis of Indanes and Indenes

Gabriele

Mancuso

Veltri

2016

Chemistry A European J

178

View full text Add to dashboard Cite

Indanes and indenes are among the most important carbocycles. Many indane and indene derivatives have shown important pharmacological activities, and the indane and indene nuclei are structural motifs present in several natural products of biological relevance. In spite of their importance, only a few reviews on their preparation methods have appeared so far in the literature, the most recent ones being published about ten years ago. The present Review is aimed at filling this gap, presenting some of the most important and innovative approaches to indanes and indenes that have been published in the course of the last ten years (coverage: from 2005 to May, 2015).

show abstract

Section: Functionalizationo Fc Yclic Precursorssupporting

confidence: 68%

“… Synthesis of 2‐(4‐ tert ‐butylcyclopenta‐1,4‐dienyl)‐1 H ‐indene 374 by Negishi‐type cross‐coupling between 2‐bromo‐1 H ‐indene 372 and LiCp t Bu 373 …”

Section: Synthesis Of Indenesmentioning

confidence: 99%

Section: Functionalizationo Fc Yclic Precursorsmentioning

confidence: 99%

Section: Synthesis Of Indenesmentioning

confidence: 99%

See 2 more Smart Citations

Recent Advances in the Synthesis of Indanes and Indenes

Gabriele

Mancuso

Veltri

2016

Chemistry A European J

178

View full text Add to dashboard Cite

show abstract

“…Elemental analyses were performed on a Perkin-Elmer 240C analyzer. 2-(tert-Butylcyclopentadienyl)-indene (1) [14] were prepared according to the literature method.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and reactivity of 2-(tert-butylcyclopentadienyl)-indenyl dinuclear ruthenium complex [η5:η5-(tBuC5H3)(C9H6)]Ru2(CO)4: Halogen induced Ru cleavage from indenyl ring

Li¹,

Tan²,

Xu³

et al. 2009

Journal of Organometallic Chemistry

View full text Add to dashboard Cite

Negishi Cross‐Coupling

2010

Comprehensive Organic Name Reactions and Reagents

View full text Add to dashboard Cite

The palladium or nickel‐catalyzed coupling between an aryl or alkenylzinc, zirconium or aluminum reagent and an alkenyl or aryl halide or triflate; specifically, it is an organozinc reagent‐mediated coupling with an alkenyl or aryl halides/triflates and is generally known as the Negishi cross‐coupling. This reaction can tolerate a variety of functional groups and commonly catalyzed by a transition metal of palladium or nickel with triaryl or trialkyl phosphines as ligands. It has also been observed that the ligand has a substantial impact on the course of the Negishi cross‐coupling. This reaction has been modified for various conditions and is applied for the formation of C‐C bonds.

show abstract

Synthesis of a novel bridged 2-(cyclopentadienyl)-indene system using Pd-catalyzed Negishi-type cross coupling

Cited by 9 publications

References 13 publications

Recent Advances in the Synthesis of Indanes and Indenes

Recent Advances in the Synthesis of Indanes and Indenes

Synthesis and reactivity of 2-(tert-butylcyclopentadienyl)-indenyl dinuclear ruthenium complex [η5:η5-(tBuC5H3)(C9H6)]Ru2(CO)4: Halogen induced Ru cleavage from indenyl ring

Negishi Cross‐Coupling

Contact Info

Product

Resources

About