Highly efficient and well-defined phosphinous acid-ligated Pd(<scp>ii</scp>) precatalysts for Hirao cross-coupling reaction

Hong, Li-Hui; Feng, Wei-Jung; Chen, Wei-Chih; Chang, Yu‐Chang

doi:10.1039/d3dt00033h

Cited by 2 publications

(1 citation statement)

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“…Implementing the concept of PNPs in these transformations, the term green process can be associated with them [ 4 ]. Thus, for example, Kumada–Tamao–Corriu [ 5 ], Mizoroki–Heck [ 6 ], Negishi [ 7 ], Stille [ 8 ], Sonogasira–Hagihara [ 9 ], Suzuki–Miyaura [ 10 , 11 ], Hiyama [ 12 ], Hirao [ 13 ] couplings, Buchwald–Hartwig reaction [ 13 ], etc., have been published using PNPs in a green manner. Another important detail in this field is the procedure employed to prepare PNPs (physical or chemical).…”

Section: Introductionmentioning

confidence: 99%

Stabilized Palladium Nanoparticles from Bis-(N-benzoylthiourea) Derived-PdII Complexes as Efficient Catalysts for Sustainable Cross-Coupling Reactions in Water

Poyraz,

Döndaş,

Belveren

et al. 2024

Molecules

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Stable palladium (II) complexes, incorporating a double (N-benzoylthiourea) arrangement bonded to a complex heterocyclic scaffold, are used as precursors of catalytic species able to promote Suzuki–Miyaura, Mizoroki–Heck, Hiyama, Buchwald–Hartwig, Hirao and Sonogashira–Hagihara cross-coupling transformations in water. These sustainable processes are chemoselective and very versatile. The nanoparticles responsible for these catalytic reactions were analyzed and studied. Their usefulness is demonstrated after several tests and analyses. The heterogeneous character of this species in water was also confirmed.

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Section: Introductionmentioning

confidence: 99%

Stabilized Palladium Nanoparticles from Bis-(N-benzoylthiourea) Derived-PdII Complexes as Efficient Catalysts for Sustainable Cross-Coupling Reactions in Water

Poyraz,

Döndaş,

Belveren

et al. 2024

Molecules

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DFT Studies on Pd/Xiao‐Phos‐Catalyzed Asymmetric Arylation of Secondary Phosphine Oxides

Liu,

Li,

Guo

et al. 2023

Eur J Org Chem

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Asymmetric arylation of secondary phosphine oxides (SPOs) has been rapidly developed, while there are few theoretical studies reported. DFT computations were carried out to study the whole catalytic cycle of Pd/Xiao‐Phos‐catalyzed asymmetric arylation of SPOs, and a modified mechanism including tautomerization and arylation was presented. Some new tautomerization mechanisms have been traversed, including base‐assisted and Pd/Xiao‐Phos‐catalyzed tautomerization. These are different from the existing report, where base‐assisted tautomerization is the most favored. The resulting intermediate enters the downstream arylation directly. Furthermore, oxidative addition is identified as the enantioselectivity‐determining step. IGMH analysis results indicate that the different non‐bonding interactions between Xiao‐Phos and SPO parts determine the enantioselectivity. This work not only provides deeper insights into the self‐adaptive property of SadPhos ligands but also offers valuable guidance for ligand design. Newly proposed tautomerization mechanisms will also bring some inspiration to subsequent related research.

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Highly efficient and well-defined phosphinous acid-ligated Pd(ii) precatalysts for Hirao cross-coupling reaction

Abstract: We report the synthesis of a new palladium complex (1a) bearing two different P-donors, di(1-adamantyl)phosphinous acid and triphenylphosphine. The heteroleptic complex with phosphinous acid ligand is rarely reported. With phenyl...

Cited by 2 publications

References 50 publications

Stabilized Palladium Nanoparticles from Bis-(N-benzoylthiourea) Derived-PdII Complexes as Efficient Catalysts for Sustainable Cross-Coupling Reactions in Water

Stabilized Palladium Nanoparticles from Bis-(N-benzoylthiourea) Derived-PdII Complexes as Efficient Catalysts for Sustainable Cross-Coupling Reactions in Water

DFT Studies on Pd/Xiao‐Phos‐Catalyzed Asymmetric Arylation of Secondary Phosphine Oxides

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