A Domino Desulfitative Coupling/Acylation/Hydration Process Cocatalyzed by Copper(I) and Palladium(II): Synthesis of Highly Substituted and Functionalized Pyrimidines

Quan, Zheng‐Jun; Hu, Wang-Hua; Jia, Xiaodong; Zhang, Zhang; Da, Yu‐Xia

doi:10.1002/adsc.201200402

Cited by 30 publications

(14 citation statements)

References 63 publications

(14 reference statements)

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“…C ‐2‐alkynyl dihydropyrimidinones (DHPMs) are bioactive pyrimidine derivatives . The Wang group sought to access C ‐2‐alkynyl DHPM derivatives 80 through a Pd/Cu I −carboxylate‐catalyzed cross‐coupling reaction between 3,4‐dihydropyrimidine‐2‐thiones 78 and terminal alkynes 24 (Scheme a) . However, to their surprise, C ‐2‐(2‐oxo‐2‐phenylethylidene)‐ N ‐3‐carbonyl‐substituted pyrimidines ( 81 ) were obtained instead of the desired products ( 80 ).…”

Section: Pd‐catalyzed Liebeskind–srogl Cross‐ Coupling Reactions (Fimentioning

confidence: 99%

The Liebeskind–Srogl Cross‐Coupling Reaction and its Synthetic Applications

et al. 2018

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The Pd-catalyzed, Cu I Àcarboxylate-mediated crosscoupling reactiono fo rganosulfur compounds with nucleophilic organometallic reagents is knowna st he Liebeskind-Srogl cross-coupling reaction. Owing to the readily available starting materials and neutral reactionc onditions, it has become an attractive procedure for the formation of carbonÀcarbon bonds, in particularf or cases in whicht radi-tional methods had failed. Since the seminal work of Liebeskind and Srogl in 2000, this reactionh as received intense attentionf rom the synthetic community.I nt his Focus Review,w eh ighlight recent advances in this intriguing cross-coupling reactiona nd its applications in organic synthesis.Scheme1.Liebeskind-Srogl cross-coupling reaction.Scheme2.The original Liebeskind-Sroglc ross-coupling reaction.d ba = dibenzylideneacetone, TFP = tri-2-furanylphosphine [a] Dr.Scheme4.Cross-coupling reaction between a-amino acid thiol esters and organostannanes. Cbz = benzyloxycarbonyl.Scheme5.Cross-coupling reaction between thiol esters and B-alkyl-9-BBN. 9-BBN = 9-borabicyclo[3.3.1]nonane.Scheme6.One-pothydroboration/intramolecular-cross-couplingr eaction between thiol esters and B-alkyl-9-BBN. DIPEA = N,N-diisopropylethylamine.Scheme7.Cross-coupling reaction between thiol esters andorganoindium reagents.Scheme8.Cross-coupling reaction between thiol esters andorganosilicon reagents. TBAF = tetra-n-butylammonium fluoride.Scheme9.Intramolecular cross-coupling reaction between thiol esters and olefins.Scheme38. Cross-coupling reaction between diaryld isulfides and boronicacids/terminal-alkynes.Scheme55. Synthesis of the C 15 ÀC 36 segment of goniodomin A. TBS = tert-butyldimethylsilyl, TBDPS = tert-butyldiphenylsilyl.Scheme56. To talsynthesis of verbenachalcone. MOM = methoxymethyl.Scheme57. Synthesis of enigmol and its stereoisomers. Boc = tert-butyloxycarbonyl.Scheme58. To talsynthesis of (À)-agelastatins A-F.Scheme59. Synthesis of quinone-containing salvinorin Aa nalogues.Scheme60. Synthesis of Soai-type aldehydes.

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Section: Pd‐catalyzed Liebeskind–srogl Cross‐ Coupling Reactions (Fimentioning

confidence: 99%

The Liebeskind–Srogl Cross‐Coupling Reaction and its Synthetic Applications

et al. 2018

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“…[59][60] In this paper, we introduce several desulfurative processes catalyzed by a woolanchored palladium(II) acetate complex ( Figure 1) under modified conditions (Scheme 1). [59][60] In this paper, we introduce several desulfurative processes catalyzed by a woolanchored palladium(II) acetate complex ( Figure 1) under modified conditions (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

Wool-anchored Pd(OAc)₂ complex: a highly active and reusable catalyst for desulfurative coupling reactions

Yang

Quan

et al. 2015

Catal. Sci. Technol.

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A biomacromolecule-anchored palladium complex, wool-Pd(OAc) 2 complex, was prepared and characterized by IR, XPS, SEM and ICP. The new complex was used as a catalyst for the Liebeskind-Srogl desulfurative coupling reactions of pyrimidin-yl thioether derivatives with terminal alkynes and aryl boronic acids, respectively. Products were isolated in moderate to excellent yields. When 10 2-(phenylthio)-1,4-dihydropyrimidine derivatives were reacted with terminal alkynes and carboxyl acids, a domino reaction process was revealed. In these reactions, this novel and efficient catalyst was capable to be reused for at least nine rounds, and performed an endurable activity as well as the wide tolerance of the substrates.Abstract: A biomacromolecule-anchored palladium complex, wool-Pd(OAc) 2 complex, was used as a catalyst for the Liebeskind-Srogl desulfurative coupling reactions of pyrimidin-yl thioether derivatives with terminal alkynes and arylboronic acids, respectively. Products were isolated in moderate to excellent yields. Notably, when 2-(phenylthio)-1,4-dihydropyrimidine derivatives were reacted with terminal alkynes and carboxyl acids, a domino reaction process was revealed. In these reactions, this novel and efficient catalyst was capable to be reused for at least nine rounds, and performed an endurable activity as well as the wide tolerance of the substrates.

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“…6,7 We have recently developed the palladium-or copper-catalyzed 30 cross-coupling reactions of aryl boronic acids, alkynes or amines with 4-aryl-pyrimidin-2-yl sulfonates as electrophiles to generate the C-C and C-N bonds. [8][9][10][11] Despite the attractive properties of many homogeneous catalysts in terms of activity and selectivity, they suffer from a number of drawbacks which lie in the removal 35 and the reuse of the catalyst, for the recycling of catalysts is also a task of great economic and environmental importance in the industry. In this context, heterogeneous catalysts are desired because of easy separation, recycling, and leaving products virtually free of palladium residues.…”

Section: Introductionmentioning

confidence: 99%

C–C/C–N cross-coupling reactions of aryl sulfonates catalyzed by an eco-friendly and reusable heterogeneous catalyst: wool–Pd complex

Yang

Quan

et al. 2015

RSC Adv.

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A well-defined heterogeneous palladium catalyst, supported on biomacromolecule, natural wool fibre, was found to be an effective catalyst for the C-C/C-N coupling of pyrimidin-2-yl sulfonates with arylboronic acids, terminal alkynes or anilines, giving the desired coupling products in good to high yields. The catalyst was characterized by XPS, IR, SEM and ICP. More importantly, the easy experimental handling catalyst is stable, shows negligible metal leaching, and can be reused for at least 10 successive runs. Undoubtedly, a wide scope of reactant, insensitive to the electron effects and the excellent coupling yields make these catalyst systems potentially useful in organic synthesis.Abstract: A well-defined heterogeneous palladium catalyst, supported on biomacromolecule, natural wool fibre, was found to be an effective catalyst for the C-C/C-N coupling of pyrimidin-2-yl sulfonates with arylboronic acids, terminal alkynes or anilines, giving the desired coupling products in good to high yields. The catalyst was characterized by XPS, IR, SEM and ICP. More importantly, the easy 10 experimental handling catalyst is stable, shows negligible metal leaching, and can be reused for at least 10 successive runs. Undoubtedly, a wide scope of reactant, insensitive to the electron effects and the excellent coupling yields make these catalyst systems potentially useful in organic synthesis.

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A Domino Desulfitative Coupling/Acylation/Hydration Process Cocatalyzed by Copper(I) and Palladium(II): Synthesis of Highly Substituted and Functionalized Pyrimidines

Cited by 30 publications

References 63 publications

The Liebeskind–Srogl Cross‐Coupling Reaction and its Synthetic Applications

The Liebeskind–Srogl Cross‐Coupling Reaction and its Synthetic Applications

Wool-anchored Pd(OAc)₂ complex: a highly active and reusable catalyst for desulfurative coupling reactions

C–C/C–N cross-coupling reactions of aryl sulfonates catalyzed by an eco-friendly and reusable heterogeneous catalyst: wool–Pd complex

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A Domino Desulfitative Coupling/Acylation/Hydration Process Cocatalyzed by Copper(I) and Palladium(II): Synthesis of Highly Substituted and Functionalized Pyrimidines

Cited by 30 publications

References 63 publications

The Liebeskind–Srogl Cross‐Coupling Reaction and its Synthetic Applications

The Liebeskind–Srogl Cross‐Coupling Reaction and its Synthetic Applications

Wool-anchored Pd(OAc)2 complex: a highly active and reusable catalyst for desulfurative coupling reactions

C–C/C–N cross-coupling reactions of aryl sulfonates catalyzed by an eco-friendly and reusable heterogeneous catalyst: wool–Pd complex

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Wool-anchored Pd(OAc)₂ complex: a highly active and reusable catalyst for desulfurative coupling reactions