Palladium-catalyzed cross-coupling reactions and electrocyclizations—efficient combinations for new cascade reactions

Meijere, Armin de; Schelper, Michael; Knoke, Mario; Yucel, Baris; Sünnemann, Hans Wolf; Scheurich, Rene Peter; Arve, Lars

doi:10.1016/j.jorganchem.2003.07.007

Cited by 33 publications

(16 citation statements)

References 36 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Several aromatic iodides can be used and the methyl acrylate ( 254 ) can have substituents. Furthermore, a functional group can be present on the cyclopropane ring, furnishing cyclopropane‐substituted products as a mixture of two isomers 124…”

Section: Versatile Building Blocks In Pd‐catalyzed Cascadesmentioning

confidence: 99%

Recent Advances in Palladium‐Catalyzed Cascade Cyclizations

2011

View full text Add to dashboard Cite

The importance of palladium‐catalyzed cross coupling reactions in contemporary organic synthesis is undisputed and underlined by the Nobel Prize for Chemistry in 2010. In addition to the highly efficient cross coupling reactions for single CC bond construction, palladium‐catalyzed cascade processes involving multiple bond formations have emerged in recent years as valuable tools for the rapid synthesis of complex molecular scaffolds. This review presents an overview of the most relevant developments in this field, with a focus on the generation of diverse poly‐ and heterocyclic scaffolds. The generally well understood reactivity of palladium has allowed the discovery of many intriguing novel cascade processes, and the creativity of the synthetic community will undoubtedly lead to many more discoveries in the future.

show abstract

Section: Versatile Building Blocks In Pd‐catalyzed Cascadesmentioning

confidence: 99%

Recent Advances in Palladium‐Catalyzed Cascade Cyclizations

2011

View full text Add to dashboard Cite

show abstract

“…201 It was shown that the reaction of bicyclopropylidene with phenyl iodide carried out in the presence of tris-(2-furyl)phosphine instead of triphenylphosphine did not lead to the corresponding phenyl-substituted diene but to a s-allyl-/p-allylpalladium complex, which could quite efficiently be trapped with various nucleophiles. The best yields for the allyl substitution products (41e95%) were obtained with amine nucleophiles, as shown in Scheme 130.…”

Section: Heck Reactionsmentioning

confidence: 99%

Recent developments in the reactivity of methylene- and alkylidenecyclopropane derivatives

Pellissier

2010

Tetrahedron

141

View full text Add to dashboard Cite

“…The latter undergo 6p -electrocyclization at elevated temperature (130 hC) to furnish the spirocyclopropanated biyclononadiene derivatives 88 (Scheme 5-22) [276]. 243 For the construction of highly condensed oligocyclic skeletons, the cascade consisting of two intramolecular Heck-type reactions and a 6p -electrocyclization as performed with the 2-bromododeca-1,11-dien-6-ynes (E)-and (Z)-89 to yield tetracycles cis-and trans-90, respectively, is particularly elegant (Scheme 5-23) [274].…”

Section: Heck-6p -Electrocyclization Cascadesmentioning

confidence: 99%

Cross‐Coupling of Organyl Halides with Alkenes: the Heck Reaction

Bräse

Meijere

2004

Metal‐Catalyzed Cross‐Coupling Reactions

View full text Add to dashboard Cite

The carbopalladation of an alkene by an organylpalladium halide is the essential step in one of the major contemporary metal-catalyzed C-C-coupling reactions. About 35 years ago, a Japanese and an American group almost simultaneously designed and executed palladium-mediated coupling reactions of aryl and alkenyl halides with alkenes [1]. In subsequent investigations, Richard Heck and his group developed this reaction into a catalytic transformation and started to demonstrate its usefulness as well as its rather broad scope. The real push to utilize this powerful C-C bond-forming process, however, started only around the mid-1980s, and by now an impressive number of publications has established the meanwhile socalled Heck reaction [2] as an indispensable method in organic synthesis [3]. The applications range from the preparation of hydrocarbons, novel polymers and dyes to new advanced enantioselective syntheses of natural products and biologically active non-natural compounds. The more or less simultaneous developments of mechanistically related variants, namely the Suzuki, Stille, Hiyama, Kumada and Negishi coupling reactions (see Chapters 2, 3, 4, 12 and 15 in this book, respectively) of metallated alkenes and arenes with aryl and alkenyl halides or the metal-catalyzed formation and cycloisomerization of enynes have drawn profit from the improvement of and mechanistic insights into the Heck reaction. This, of course, also applies vice versa. Using only a catalytic amount of a palladium(0) complex or a precursor to a palladium species, the Heck reaction can bring about unprecedented structural changes, particularly when conducted intramolecularly. The full potential of this palladium-catalyzed process is still being further explored, as demonstrated by a total of 2400 relevant publications during the past 10 years, and a continuous annual growth in publications of 15 % per year. Therefore, it is appropriate to say that the Heck reaction is one of the true "power tools" in contemporary organic synthesis [4], competing favorably with the Diels-Alder reaction (25 000 references), olefin metathesis (1500 references), Wittig reaction (15 000 references), or Claisen rearrangement (15 000 references). Scheme 5-1 Mechanism of the Heck reaction [7]. Pd(OTfa) 2 , P(2-furyl) 3 , iPr 2 EtN; Pd(OTfa) 2 or Pd(F 6 -acac) 2 ] and fluorinated phosphanes [90] [91]

show abstract

Palladium-catalyzed cross-coupling reactions and electrocyclizations—efficient combinations for new cascade reactions

Cited by 33 publications

References 36 publications

Recent Advances in Palladium‐Catalyzed Cascade Cyclizations

Recent Advances in Palladium‐Catalyzed Cascade Cyclizations

Recent developments in the reactivity of methylene- and alkylidenecyclopropane derivatives

Cross‐Coupling of Organyl Halides with Alkenes: the Heck Reaction

Contact Info

Product

Resources

About