Selective Preparation of Complex Polycyclic Molecules from Acyclic Precursors via Radical Mediated- or Transition Metal-Catalyzed Cascade Reactions

Malacrìa, Max

doi:10.1021/cr9500186

Cited by 417 publications

(76 citation statements)

References 143 publications

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“…The ratio 16 a/16 b is itself dependant on the nature of the ligands coordinated to the palladium center. As an example, [Pd(PPh 3 ) 2 ](OAc) 2 and Pd(OAc) 2 lead to regioisomeric ratios of 1:2.9 and 1:16.9, respectively.…”

Section: Reviewsmentioning

confidence: 99%

“…In the course of earlier investigations on the cycloisomerization of enynes, Trost and Rise [32] reported the reaction of enyne 7 with a system consisting of [Pd 2 (dba) 3 ], P(o-Tol) 3 , and acetic acid in the presence of 10 equivalents of polymethylhydrosiloxane (PMHS) at room temperature in benzene. Product 56 was obtained in 96 % yield as a single isomer [Eq.…”

Section: Palladium-catalyzed Reductive Cyclizationsmentioning

confidence: 99%

“…Moreover, the development of tandem reactions and rearrangements to construct organic polyfunctional frameworks through the formation of carbon-hydrogen, carbon-carbon, or carbon-heteroatom bonds constitutes a prime issue for organic chemists. [3] This Review does not aim to cover all the possible rearrangements, as some reviews published in recent years have focused on general and specific reorganization reactions. [4,5] The latest discoveries will be placed within a historical context, but the main thrust is to highlight the new possibilities that metal-catalyzed cycloisomerization reactions currently offer to the synthetic chemist.…”

Section: Introductionmentioning

confidence: 99%

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Cycloisomerization of 1,n‐Enynes: Challenging Metal‐Catalyzed Rearrangements and Mechanistic Insights

Michelet¹,

Toullec²,

Genêt³

2008

Angew Chem Int Ed

950

248

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Metal-catalyzed cycloisomerization reactions of 1,n-enynes have appeared as conceptually and chemically highly attractive processes as they contribute to the highly demanded search for atom economy and allow the discovery of new reactions. Since the pioneering studies with palladium by the research group of Barry Trost in the mid-1980s, several other metals have been identified as excellent catalysts for the rearrangement of enyne skeletons. Moreover, the behavior of 1,n-enynes may be influenced by other functional groups such as alcohols, aldehydes, ethers, alkenes, or alkynes, thus enhancing the molecular complexity of the synthesized products. Apart from the intrinsic rearrangements of 1,n-enynes, several tandem reactions incorporating intramolecular trapping agents or intermolecular partners have been discovered. This Review aims to highlight the main contributions in this field of catalysis and to propose and comment on the mechanistic insights of the recent discoveries.

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Section: Reviewsmentioning

confidence: 99%

Section: Palladium-catalyzed Reductive Cyclizationsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Cycloisomerization of 1,n‐Enynes: Challenging Metal‐Catalyzed Rearrangements and Mechanistic Insights

Michelet¹,

Toullec²,

Genêt³

2008

Angew Chem Int Ed

950

248

View full text Add to dashboard Cite

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“…[62][63][64] Of these, cyclic cascade carbopalladations [65][66][67][68] have gained wide acceptance and have become a rapidly growing area in synthetic organic chemistry because of their increasing synthetic efficiency. In this context, we developed a novel palladium-mediated successive reaction providing a new general route to benzo-and naphthohydrindans 37 and 38, respectively.…”

Section: Successive Ring Expansion-insertion Reactionmentioning

confidence: 99%

Synthetic Organic Chemistry Based on Small Ring Compounds

Nemoto

2007

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…A particular advantage of OPEN ACCESS these concepts is the huge increase in structural complexity facilitated by the use of even the simplest starting materials. This is also one of the driving factors for constant research advancements in this field [5][6][7][8][9][10][11][12][13][14][15][16][17].…”

Section: Introductionmentioning

confidence: 99%

Sequentially Palladium-Catalyzed Processes in One-Pot Syntheses of Heterocycles

Lessing

Müller

2015

Applied Sciences

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Sequentially Pd-catalyzed processes are excellent entries to heterocycle synthesis. The broad mechanistic variety combined with often very mild reaction conditions allow the concatenation of elementary organic and organometallic steps to novel sequences in the sense of one-pot domino and multicomponent reactions. Given the numerous opportunities of alkyne coordination and their Pd-mediated transformations, alkynylation and carbometallation play a key role, both for purely organometallic sequences as well as in those processes that are intercepted by cyclocondensation. Pd-catalyzed aminations also find more and more entry into novel heterocycle syntheses based upon this theme.

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Selective Preparation of Complex Polycyclic Molecules from Acyclic Precursors via Radical Mediated- or Transition Metal-Catalyzed Cascade Reactions

Cited by 417 publications

References 143 publications

Cycloisomerization of 1,n‐Enynes: Challenging Metal‐Catalyzed Rearrangements and Mechanistic Insights

Cycloisomerization of 1,n‐Enynes: Challenging Metal‐Catalyzed Rearrangements and Mechanistic Insights

Synthetic Organic Chemistry Based on Small Ring Compounds

Sequentially Palladium-Catalyzed Processes in One-Pot Syntheses of Heterocycles

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