Desulfitative Cross-Coupling of Protecting Group-Free 2-Thiouracil Derivatives with Organostannanes

Sun, Qi; Suzenet, Franck; Guillaumet, Gérald

doi:10.1021/jo1003482

Cited by 33 publications

(8 citation statements)

References 31 publications

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“…[34][35][36][37] Similarly, 2-thiouracil has been coupled with, e.g., 2-furyltributylstannane to 2-furyl-2pyrimidin-4-one. 38 As two structures have been suggested for the P 4 S 10 -pyridine reagent we have also performed an X-ray study, which gave conclusive evidence for structure 3. A somewhat related structure, namely 10, has been determined by Meisel et al (Figure 2).…”

Section: ' Results and Discussionmentioning

confidence: 81%

Thionations Using a P₄S₁₀−Pyridine Complex in Solvents Such as Acetonitrile and Dimethyl Sulfone

et al. 2011

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Tetraphosphorus decasulfide (P(4)S(10)) in pyridine has been used as a thionating agent for a long period of time. The moisture-sensitive reagent has now been isolated in crystalline form, and the detailed structure has been determined by X-ray crystallography. The thionating power of this storable reagent has been studied and transferred to solvents such as acetonitrile in which it has proven to be synthetically useful and exceptionally selective. Its properties have been compared with the so-called Lawesson reagent (LR). Particularly interesting are the results from thionations at relatively high temperatures (∼165 °C) in dimethyl sulfone as solvent. Under these conditions, for instance, acridone and 3-acetylindole could quickly be transformed to the corresponding thionated derivatives. Glycylglycine similarly gave piperazinedithione. At these temperatures, LR is inefficient due to rapid decomposition. The thionated products are generally cleaner and more easy to obtain because in the crystalline reagent, impurities which invariably are present in the conventional reagents, P(4)S(10) in pyridine or LR, have been removed.

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Section: ' Results and Discussionmentioning

confidence: 81%

Thionations Using a P₄S₁₀−Pyridine Complex in Solvents Such as Acetonitrile and Dimethyl Sulfone

et al. 2011

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“…The Guillaumet group independently reported a similar cross‐coupling reaction of 2‐thiouracil derivatives 74 and 75 with organostannanes 7 (Scheme ), which avoided the need for tedious protection/deprotection of the acyl thiourea moiety (−NH−C(S)−NH−C(O)−). Interestingly, the Cu I species seemed to be very important for the coupling reaction, whereas the carboxylate counterions were not necessary, very different to the previously published cases.…”

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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“…Subsequently, Suzenet and co-workers 16 have reported a similar strategy for the efficient cross-coupling of thiouracil derivatives bearing a latent thiol group. However, using the previously reported method developed by Kappe and co-workers, the reactions met with failure when coupling 2-thiouracil with phenylboronic acid.…”

Section: Use Of Unsaturated Heteroarene Thioethersmentioning

confidence: 99%

Transition metal-catalyzed C–C bond formation via C–S bond cleavage: an overview

2013

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Transition metal-catalyzed C-C bond formations have been well studied over the last four decades. An improved mechanistic understanding of such reactions has helped chemists to develop further improvements, modifications and even new reactions. In the area of transition metal-catalyzed cross-coupling reactions the C-S bond cleaving reactions have attracted a lot of attention in the last decade as they provide a good alternative to the use of organo-halide reagents in traditional cross-coupling reactions. The availability of a wide range of organo-sulfur species provides the opportunity for developing different transformations for the synthesis of interesting organic compounds. This tutorial review focuses on recent examples of the transition metal-catalyzed C-C bond forming reactions using organo-sulfur species.

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Desulfitative Cross-Coupling of Protecting Group-Free 2-Thiouracil Derivatives with Organostannanes

Abstract: We here report a unique and efficient copper bromide mediated pallado-catalyzed coupling of protecting group-free 2-thiouracil derivatives with organostannanes. The nature of the copper appears to be crucial for successful cross coupling.

Cited by 33 publications

References 31 publications

Thionations Using a P₄S₁₀−Pyridine Complex in Solvents Such as Acetonitrile and Dimethyl Sulfone

Thionations Using a P₄S₁₀−Pyridine Complex in Solvents Such as Acetonitrile and Dimethyl Sulfone

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

Transition metal-catalyzed C–C bond formation via C–S bond cleavage: an overview

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Desulfitative Cross-Coupling of Protecting Group-Free 2-Thiouracil Derivatives with Organostannanes

Abstract: We here report a unique and efficient copper bromide mediated pallado-catalyzed coupling of protecting group-free 2-thiouracil derivatives with organostannanes. The nature of the copper appears to be crucial for successful cross coupling.

Cited by 33 publications

References 31 publications

Thionations Using a P4S10−Pyridine Complex in Solvents Such as Acetonitrile and Dimethyl Sulfone

Thionations Using a P4S10−Pyridine Complex in Solvents Such as Acetonitrile and Dimethyl Sulfone

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

Transition metal-catalyzed C–C bond formation via C–S bond cleavage: an overview

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Product

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Thionations Using a P₄S₁₀−Pyridine Complex in Solvents Such as Acetonitrile and Dimethyl Sulfone

Thionations Using a P₄S₁₀−Pyridine Complex in Solvents Such as Acetonitrile and Dimethyl Sulfone