Palladium-catalyzed [3 + 2] cycloaddition reaction using 2-(sulfonylmethyl)- or 2-(cyanomethyl)allyl carbonate

1984 ◽  
Vol 25 (45) ◽  
pp. 5183-5186 ◽  
Author(s):  
Isao Shimizu ◽  
Yukihiro Ohashi ◽  
Jiro Tsuji
Keyword(s):  
Cycloaddition Reaction ◽  
Palladium Catalyzed

scholarly journals Palladium-Catalyzed [3+2] Cycloaddition via Two-Fold 1,3-C(sp3)−H Activation

2020 ◽  
Author(s):  
Hojoon Park ◽  
jin-quan yu
Keyword(s):  
Functional Groups ◽  
Sulfonic Acid ◽  
Cycloaddition Reaction ◽  
Wide Range ◽  
Leaving Group ◽  
Palladium Catalyzed ◽  
Directing Group ◽  
Overall Efficiency ◽  
Weak Coordination ◽  
Single Reaction

<div>Cycloaddition reactions provide an expeditious route to construct ring systems in a highly convergent and stereoselective manner. For a typical cycloaddition reaction to occur, however, the installation of multiple reactive functional groups (π-bonds, leaving group, etc.) are required within the substrates, compromising the overall efficiency or scope of the cycloaddition reaction. Here, we report a palladium-catalyzed [3+2] reaction that utilizes C(sp<sup>3</sup>)–H activation to generate the three-carbon unit for formal cycloaddition with maleimides. We implemented a strategy where the initial C(sp<sup>3</sup>)–H activation/olefin insertion would trigger a relayed, second remote C(sp<sup>3</sup>)–H activation to complete a formal [3+2] cycloaddition. The diastereoselectivity profile of this reaction resembles that of a typical pericyclic cycloaddition reaction in that the relationships between multiple stereocenters are exquisitely controlled in a single reaction. The key to success was the use of weakly coordinating amides as the directing group, as undesired Heck or alkylation pathways were preferred with other types of directing groups. The use of the pyridine-3-sulfonic acid ligands is critical to enable C(sp<sup>3</sup>)–H activation directed by this weak coordination. The method is compatible with a wide range of amide substrates, including lactams, which lead to novel spiro-bicyclic products. The [3+2] product is also shown to undergo a reductive desymmetrization process to access chiral cyclopentane bearing multiple stereocenters with excellent enantioselectivity.</div>

Palladium-catalyzed [4 + 3] dearomatizing cycloaddition reaction of N-iminoquinolinium ylides

2020 ◽  
Vol 7 (18) ◽  
pp. 2612-2617
Author(s):  
Wenhao Dai ◽  
Chunpu Li ◽  
Yichu Liu ◽  
Xu Han ◽  
Xingjun Li ◽  
...  
Keyword(s):  
Functional Group ◽  
Cycloaddition Reaction ◽  
Membered Ring ◽  
Efficient Approach ◽  
Mild Conditions ◽  
Palladium Catalyzed

An efficient approach to obtain saturated seven-membered ring containing three heteroatoms has been developed by using a palladium-catalyzed [4 + 3] dearomatizing cycloaddition. This approach features mild conditions and good functional group tolerance.

One-Step Synthesis of Oxodimethylenemethane−Transition Metal Complexes and Palladium-Catalyzed Cycloaddition Reaction

1996 ◽  
Vol 61 (15) ◽  
pp. 4971-4974 ◽  
Author(s):  
Isao Ikeda ◽  
Akihiro Ohsuka ◽  
Kazuyoshi Tani ◽  
Toshikazu Hirao ◽  
Hideo Kurosawa
Keyword(s):  
Transition Metal ◽  
Metal Complexes ◽  
Transition Metal Complexes ◽  
Cycloaddition Reaction ◽  
Palladium Catalyzed ◽  
One Step

scholarly journals Palladium-Catalyzed Bisdiene Carbocyclizations: A Facile [3 + 2] Cycloaddition Reaction Mode.

ChemInform ◽  
2004 ◽  
Vol 35 (12) ◽  
Author(s):  
James M. Takacs ◽  
Alexei P. Leonov
Keyword(s):  
Cycloaddition Reaction ◽  
Palladium Catalyzed

scholarly journals Synergistic Palladium-Phosphoric Acid Catalysis in (3 + 2) Cycloaddition Reactions between Vinylcyclopropanes and Imines

Catalysts ◽  
2020 ◽  
Vol 10 (2) ◽  
pp. 150 ◽  
Author(s):  
Vasco Corti ◽  
Enrico Marcantonio ◽  
Martina Mamone ◽  
Alessandro Giungi ◽  
Mariafrancesca Fochi ◽  
...  
Keyword(s):  
Phosphoric Acid ◽  
Palladium Catalyst ◽  
Palladium Catalysts ◽  
Acid Catalysis ◽  
Cycloaddition Reaction ◽  
Cross Coupling ◽  
Cycloaddition Reactions ◽  
Synergistic Catalysis ◽  
Palladium Catalyzed ◽  
First Time

The palladium-catalyzed (3 + 2) cycloaddition reaction between vinylcyclopropanes (VCPs) bearing geminal EWG’s and imines represents a straightforward and flexible entry to polysubstituted pyrrolidine derivatives. In this paper, we demonstrate that using a synergistic catalysis approach, based on the combination of phosphoric acid and palladium catalysts, it is possible to engage for the first time N-aryl and N-benzyl imines in this cycloaddition reaction. A range of polysubstituted pyrrolidines is obtained with moderate to good yields and diastereoselectivities, using a simple palladium species (Pd(PPh3)4) and an archetypical phosphoric acid as catalyst combination. A two-step scheme which exploits the same palladium catalyst for two consecutive and mechanistically distinct reactions (the cycloaddition and a Suzuki–Miyaura cross-coupling) is also presented. This synergistic catalysis approach is well posited for the development of the enantioselective version of this reaction. A screening of common BINOL-derived chiral phosphoric acids as catalyst component identified a species giving the product with moderate, yet promising, enantioselectivity (64% ee).

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