A General Regioselective Synthesis of 2,4-Diarylpyrimidines from 2- Thiouracil through Two Orthogonal Cross-Coupling Reactions

Čerňová, Miroslava; Pohl, Radek; Klepetářová, Blanka; Hocek, Michal

doi:10.1055/s-0031-1290826

Cited by 9 publications

(1 citation statement)

References 8 publications

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“…The reaction was proved to tolerate different substitutions on the pyrimidine scaffold and both electron-poor and electron-rich boronic acids as coupling partners in the presence of relatively inexpensive Pd(OAc) 2 as a precatalyst, PPh 3 as a ligand and CuTC as a co-catalyst under irradiation conditions for 1 h (Scheme 53) [115,116]. Similarly, arylation of functionalized 2-methylthiopyrimidine [117] and 4-phenylthiopyrimidine [118] derivatives with boronic acids were reported recently under microwave irradiation conditions.…”

Section: Liebeskind-srogl Cross-coupling Reactionmentioning

confidence: 99%

Microwave-Assisted Palladium-Catalyzed Cross-Coupling Reactions: Generation of Carbon–Carbon Bond

Salih

Baqi

2019

Catalysts

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Cross-coupling reactions furnishing carbon–carbon (C–C) bond is one of the most challenging tasks in organic syntheses. The early developed reaction protocols by Negishi, Heck, Kumada, Sonogashira, Stille, Suzuki, and Hiyama, utilizing palladium or its salts as catalysis have, for decades, attracted and inspired researchers affiliated with academia and industry. Tremendous efforts have been paid to develop and achieve more sustainable reaction conditions, such as the reduction in energy consumption by applying the microwave irradiation technique. Chemical reactions under controlled microwave conditions dramatically reduce the reaction time and therefore resulting in increase in the yield of the desired product by minimizing the formation of side products. In this review, we mainly focus on the recent advances and applications of palladium catalyzed cross-coupling carbon–carbon bond formation under microwave technology.

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Section: Liebeskind-srogl Cross-coupling Reactionmentioning

confidence: 99%

Microwave-Assisted Palladium-Catalyzed Cross-Coupling Reactions: Generation of Carbon–Carbon Bond

Salih

Baqi

2019

Catalysts

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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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Dichloroimidazolidinedione‐activated one‐pot Suzuki–Miyaura cross‐coupling of phenols

Madankar

Mokhtari

Mirjafary

2020

Applied Organom Chemis

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The first general method for the Suzuki‐type cross‐coupling of phenols with aryl boronic acids using dichloroimidazolidinedione (DCID) as a new reagent is presented. In the presence of DCID and Pd/metal–organic framework (MOF), coupling of aryl boronic acids with a wide range of phenols, was carried out smoothly in tetrahydrofuran (THF) at reflux conditions to afford the cross‐coupling products in good to excellent yields. The structures of all compounds were corroborated by 1H‐ and 13C‐NMR. A plausible mechanism for this type of reaction is proposed.

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A General Regioselective Synthesis of 2,4-Diarylpyrimidines from 2- Thiouracil through Two Orthogonal Cross-Coupling Reactions

Abstract: A novel efficient synthesis of 2,4-diarylpyrimidines was developed based on phosphonium-mediated Suzuki coupling of 2-(methylsulfanyl)pyrimidin-4(3H)-one (at position 4) followed by the Liebeskind-Srogl cross-coupling (at position 2) under microwave irradiation.

Cited by 9 publications

References 8 publications

Microwave-Assisted Palladium-Catalyzed Cross-Coupling Reactions: Generation of Carbon–Carbon Bond

Microwave-Assisted Palladium-Catalyzed Cross-Coupling Reactions: Generation of Carbon–Carbon Bond

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

Dichloroimidazolidinedione‐activated one‐pot Suzuki–Miyaura cross‐coupling of phenols

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