Palladium-Catalyzed Difunctionalization of Norbornenes via Arylation and Alkynylation

Shi, Yijun; Ji, Chong‐Lei; Liu, Chengwei

doi:10.1021/acs.joc.2c02295

Cited by 3 publications

(2 citation statements)

References 54 publications

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“…In 2023, Ji and Liu expanded on the Pd-catalyzed three-component arylalkynylation of oxabenzonorbornadiene derivatives ( Scheme 43 ) [ 94 ]. Initially reported by Liu and co-workers in 2006 [ 95 ], present conditions were altered to avoid aqueous NaOH, opting for Cs 2 CO 3 .…”

Section: Reviewmentioning

confidence: 99%

Transition-metal-catalyzed domino reactions of strained bicyclic alkenes

Pounder¹,

Neufeld²,

Myler³

et al. 2023

Beilstein J. Org. Chem.

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This review presents a comprehensive overview of transition-metal-catalyzed domino reactions of strained bicyclic alkenes, including both homo- and heterobicyclic alkenes. These compounds are important synthons in organic synthesis, providing an important platform for the construction of biologically/medicinally significant compounds which bear multiple stereocenters. The review has been divided according to the metal used in the reaction. An overview of the substrate scope, reaction conditions, and their potential applications in organic synthesis is discussed. A comprehensive outlook on the reactivity paradigms of homo- and heterobicyclic alkenes is discussed and should shed light on future directions for further development in this field.

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Section: Reviewmentioning

confidence: 99%

Transition-metal-catalyzed domino reactions of strained bicyclic alkenes

Pounder¹,

Neufeld²,

Myler³

et al. 2023

Beilstein J. Org. Chem.

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“…The insertion of an alkene into the aryl–Ni bond caused the observed selectivity. Additionally, the employment of strained norbornenes (NBEs) indicates an alternative strategy upon palladium catalysts, mainly due to their restricted conformation capable of blocking β-hydride elimination (Scheme a, II). Therefore, developing more efficient and practical methods for the alkynylarylation of simple alkenes is highly desirable.…”

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confidence: 99%

Palladium-Catalyzed 1,2-Alkynylarylation of Vinyl Arenes with Haloalkynes and Arylboronic Acids

Ma,

Fang,

Jiang

et al. 2024

Org. Lett.

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We herein disclose a novel palladium-catalyzed 1,2-alkynylarylation of vinyl arenes using haloalkynes and arylboronic acids as coupling partners. This reaction is characterized by broad substrate scope, controllable reaction sequence, and excellent chemo-and regioselectivities. Mechanistic investigations suggest that the reaction is initiated by regioselective insertion of vinyl arenes into the alkynyl-Pd(II) species, and the silver salt is crucial for this transformation, serving as both the Lewis acid and halide scavenger. This protocol provides efficient access to new carbon skeletons, which are embedded in the key biologically active motifs.

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Base/Solvent Controlled Divergent Synthesis of Norbornane-Fused Dihydrophenanthrenes and Triphenylenes via Palladium Catalyst

Dehghan,

Ghasemi,

Jafarpour

et al. 2023

Org. Lett.

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A base/solvent controlled divergent synthesis for the construction of polycyclic hydrocarbons has been developed. In this process, norbornene through a reagent role leads to the synthesis of norbornane-fused dihydrophenanthrenes, which are essential due to their biological activities. Amazingly, by switching solvent and base, the role of norbornene becomes limited to a mediator/catalyst; therefore, it is removed from the final scaffold, and triphenylenes are regioselectively synthesized. Additionally, by removing norbornene from the reaction conditions, a different path leading to synthesis of unsymmetrically substituted triphenylenes with exceptional regioselectivity is established. This reaction includes a rare domino decarboxylation/C−H activation/annulation in a chemo-and regioselective manner.

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Palladium-Catalyzed Difunctionalization of Norbornenes via Arylation and Alkynylation

Cited by 3 publications

References 54 publications

Transition-metal-catalyzed domino reactions of strained bicyclic alkenes

Transition-metal-catalyzed domino reactions of strained bicyclic alkenes

Palladium-Catalyzed 1,2-Alkynylarylation of Vinyl Arenes with Haloalkynes and Arylboronic Acids

Base/Solvent Controlled Divergent Synthesis of Norbornane-Fused Dihydrophenanthrenes and Triphenylenes via Palladium Catalyst

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