Palladium‐catalyzed Cascade Reactions of Alkenes, Alkynes, and Allenes

Gao, Hongyin; Zhang, Junliang

doi:10.1002/9781118356654.ch6

Cited by 2 publications

(1 citation statement)

References 215 publications

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“…The myriad of chemical reactivities exhibited by palladium catalysis allow the creation of strained and high energy structures rivaling that of any other organic transformation. − As a result, palladium catalysis has been applied to the synthesis of a variety of strained small rings. , Cascade sequences, , such as palladium-catalyzed cross-coupling/electrocyclization cascades, , quickly increase molecular complexity. Cross-coupling reactions typically require elevated temperature conditions which can preclude their use to study strained structures, but we report herein an approach that enables synthesis of metastable compounds and the study of their subsequent reactivities.…”

Section: Introductionmentioning

confidence: 99%

Using Ring Strain to Control 4π-Electrocyclization Reactions: Torquoselectivity in Ring Closing of Medium-Ring Dienes and Ring Opening of Bicyclic Cyclobutenes

et al. 2017

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Syntheses of strained cyclic dienes were accomplished via palladium(II)-catalyzed oxidative cyclizations of terminal bis(vinylboronate esters). The reactions generate strained (E,E)-1,3-dienes that undergo spontaneous 4π-electrocyclizations to form bicyclic cyclobutenes. Formation of the cyclobutenes is driven by the strain in the medium-ring (E,E)-1,3-diene intermediate. Thermal ring openings of the cyclobutenes give (Z,Z)-1,3-diene products, again for thermodynamic reasons. DFT calculations verified the thermodynamic versus kinetic control of the reactions, and kinetic studies are in excellent agreement with the calculated energy changes. An extension of the tandem coupling/4π-electrocyclization pathway was demonstrated by a palladium(II)-catalyzed oxidative homocoupling/8π-electrocyclization cascade.

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Section: Introductionmentioning

confidence: 99%

Using Ring Strain to Control 4π-Electrocyclization Reactions: Torquoselectivity in Ring Closing of Medium-Ring Dienes and Ring Opening of Bicyclic Cyclobutenes

et al. 2017

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Organoselenium Catalyzed Electrochemical Cascade Cyclization: An Access to Naphthofuran‐2‐carboxaldehyde

Dagar,

Singh,

Raha Roy

2024

Adv Synth Catal

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We have developed an approach for the construction of naphthofuran‐2‐carboxaldehyde derivatives by utilizing the synergy of electrochemical oxidation and organo‐selenium catalysis at room temperature. The compatibility of various functional groups and scalability of this protocol demonstrate the practicality of the electrochemical strategy. The synthetic utility of this strategy is furthermore demonstrated by synthesizing diversified molecules through downstream transformations.

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Palladium‐catalyzed Cascade Reactions of Alkenes, Alkynes, and Allenes

Cited by 2 publications

References 215 publications

Using Ring Strain to Control 4π-Electrocyclization Reactions: Torquoselectivity in Ring Closing of Medium-Ring Dienes and Ring Opening of Bicyclic Cyclobutenes

Using Ring Strain to Control 4π-Electrocyclization Reactions: Torquoselectivity in Ring Closing of Medium-Ring Dienes and Ring Opening of Bicyclic Cyclobutenes

Organoselenium Catalyzed Electrochemical Cascade Cyclization: An Access to Naphthofuran‐2‐carboxaldehyde

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