Pd(II)-Catalyzed Asymmetric Oxidative 1,2-Diamination of Conjugated Dienes with Ureas

Wu, Min-Song; Fan, Tongxiang; Chen, Shusen; Han, Zhi‐Yong; Gong, Liu‐Zhu

doi:10.1021/acs.orglett.8b00870

Cited by 52 publications

(25 citation statements)

References 72 publications

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“…When dialkylureas were used, a different pathway occurred, affording 4-vinylimidazolidin-2-ones via a diamination process. 58 The reaction was completely regioselective, with the new C-C bond being created at the terminal C=C bond of the diene.…”

Section: Scheme 38 Intermolecular Allylation Of Aminesmentioning

confidence: 99%

π-Allylpalladium Complexes in Synthesis: An Update

Parisotto¹,

Deagostino²

2019

Synthesis

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This review aims to summarize the development of the chemistry of π-allylpalladium complexes both as intermediates and catalysts/reagents between 2013 and early 2109. Major attention has been devoted to the synthetic aspect of these versatile intermediates.1 Introduction2 π-Allylpalladium Complexes Generated from Allyl Electrophiles2.1 Activated Allylic Compounds2.2 Unactivated Allylic Compounds: Allylic Alcohols and Hydrocarbons2.3 Total Syntheses3 π-Allylpalladium Complexes Generated from Dienes3.1 Conjugated Dienes3.2 Allenes4 π-Allylpalladium Complexes Exploited as Reactants and Precatalysts4.1 Allylpalladium-Catalyzed Dehydrogenation4.2 Allylpalladium-Catalyzed Synthesis of Alkenylboronic Esters4.3 Allylpalladium-Based Precatalysts5 Conclusions

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Section: Scheme 38 Intermolecular Allylation Of Aminesmentioning

confidence: 99%

π-Allylpalladium Complexes in Synthesis: An Update

Parisotto¹,

Deagostino²

2019

Synthesis

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“…This non-asymmetric transformation was carried out without additional ligands, and led to vinyl imidazolidinones in good to excellent yields. Very recently, a highly efficient synthesis of chiral imidazolidin-2-ones through the Pd(II)catalyzed diamination of 1,3-dienes with 1,3-dialkylureas has been reported by Gong and Han (Scheme 26) [112]. High yields and excellent enantioselectivities were achieved under mild reaction conditions by means of a chiral pyridine-oxazoline ligand.…”

Section: Metal-catalyzed Intermolecular Diamination Of Dienes With Ureasmentioning

confidence: 99%

“…Molecular sieves were found to improve both the yield and enantioselectivity values. Notably, as for the non-asymmetric transformation [110], this enantioselective diamination reaction involves exclusively the terminal C=C double bond of 1,3-dienes, and for this, it is highly complementary to the asymmetric Shi's protocol [112], which mainly occurs at the internal double bond (Scheme 29).…”

Section: Metal-catalyzed Intermolecular Diamination Of Dienes With Ureasmentioning

confidence: 99%

“…Pd-catalyzed intermolecular asymmetric diamination of 1,3-dienes to chiral imidazolidin-2-ones [112].…”

Section: Scheme 26mentioning

confidence: 99%

“…An asymmetric version of this diamination process was subsequently disclosed. (E)-1,3-Hexadiene and di-tert-butyldiaziridinone were used as model substrates, while Pd2(dba)3 and several chiral ligands were examined (Scheme 29) [112]. The choice of the ligand was critical in order to achieve high conversion and enantioselectivity.…”

Section: Metal-catalyzed Intermolecular Diamination Of Alkenes With Dmentioning

confidence: 99%

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Recent Advances in the Catalytic Synthesis of Imidazolidin-2-ones and Benzimidazolidin-2-ones

et al. 2019

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2-Imidazolidinone and its analogues are omnipresent structural motifs of pharmaceuticals, natural products, chiral auxiliaries, and intermediates in organic syntheses. Over the years, continuous efforts have been addressed to the development of sustainable and more efficient protocols for the synthesis of these heterocycles. This review gives a summary of the catalytic strategies to access imidazolidin-2-ones and benzimidazolidin-2-ones that have appeared in the literature from 2010 to 2018. Particularly important contributions beyond the timespan will be mentioned. The review is organized in four main chapters that identify the most common approaches to imidazolidin-2-one derivatives: (1) the direct incorporation of the carbonyl group into 1,2-diamines, (2) the diamination of olefins, (3) the intramolecular hydroamination of linear urea derivatives and (4) aziridine ring expansion. Methods not included in this classification will be addressed in the miscellaneous section.

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Cobalt(III)‐Catalyzed Aerobic Diamination of α‐Alkyl Styrenes with Anilines

Yang

2023

Adv Synth Catal

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A commercially available cobalt complex Cp*Co III (CO)I 2 has been found to effectively catalyze the diamination of α-alkyl styrenes with anilines under a mild reaction condition, using dioxygen as the oxidant. This reaction features a reasonably good substrate scope of amines and a good functional group tolerance. Preliminary mechanistic studies have shown that Cp*Co III (CO)I 2 alone can promote the diamination reaction.

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Pd(II)-Catalyzed Asymmetric Oxidative 1,2-Diamination of Conjugated Dienes with Ureas

Cited by 52 publications

References 72 publications

π-Allylpalladium Complexes in Synthesis: An Update

π-Allylpalladium Complexes in Synthesis: An Update

Recent Advances in the Catalytic Synthesis of Imidazolidin-2-ones and Benzimidazolidin-2-ones

Cobalt(III)‐Catalyzed Aerobic Diamination of α‐Alkyl Styrenes with Anilines

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