Generation of diverse 2-pyrones via palladium-catalyzed site-selective Suzuki-Miyaura couplings of 3-bromo-4-tosyloxy-2-pyrone

Lei, Xiaoli; Gao, Liang; Ding, Qiuping; Peng, Yiyuan; Wu, Jie

doi:10.1039/c1ob05783a

Cited by 18 publications

(5 citation statements)

References 68 publications

(2 reference statements)

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“…In a complementary exploration of C-3 functionalisation 5a was brominated (Br 2 , CHCl 3 , 72 h, reflux) to afford 7 in 73% yield. Guided by reaction conditions employed by Wu et al, for the 3-arylation of 3-bromopyran-2-ones 23 the Suzuki crosscoupling of 7 with arylboronic acids gave 6a (40%), 6b (58%) and 6c (36%) (unoptimized yields); it is noteworthy that the highest yield for the Suzuki cross-coupling reaction was recorded with the electron rich 4-methoxyphenylboronic acid and complements the C-H bond functionalisation where the best yield was noted for electron deficient coupling partners. Bromination of 5b was marginally more effective, though did require the addition of pyridine (0.25 eq.)…”

Section: Resultsmentioning

confidence: 99%

Synthesis, C–H bond functionalisation and cycloadditions of 6-styryl-1,2-oxathiine 2,2-dioxides

et al. 2021

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Section: Resultsmentioning

confidence: 99%

Synthesis, C–H bond functionalisation and cycloadditions of 6-styryl-1,2-oxathiine 2,2-dioxides

et al. 2021

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“…Lei et al. have reported that 3‐bromo‐6‐methyl‐4‐tosyloxy‐2‐pyrone undergoes Pd 2 (dba) 3 /Johnphos‐catalyzed chemoselective C‐3 arylation with arylboronic acids and that the resulting cross‐coupling products provide 3,4‐diaryl‐6‐methyl‐2‐pyrones bearing different aryl groups in good overall yields by Pd(OAc) 2 /PCy 3 ‐catalyzed Suzuki–Miyaura cross‐coupling reactions with different arylboronic acids 213…”

Section: Discussionmentioning

confidence: 99%

Selective Palladium‐Catalyzed Suzuki–Miyaura Reactions of Polyhalogenated Heteroarenes

2012

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The palladium-catalyzed Suzuki-Miyaura reaction of multiply halogenated, electron-rich and electron-deficient heteroarenes is one of the most reliable and environmentally friendly tools for installing a wide range of non-functionalized and functionalized carbon substituents onto heteroaromatic systems with exquisite chemo-and site-selectivity. For substrates with different halogen groups the chemoselectivity of the Suzuki-Miyaura reactions has been found to be dependent on the reactivity difference between the halogens. However, the hardest achievement of selectivity in Suzuki-Miyaura monocouplings involving polyhalogenated heteroarenes with identical halogen atoms has been shown to be dominated by steric and electronic effects and the presence of directing groups at positions neighbouring the reaction sites. Moreover, in the case of symmetrically substituted dihaloheteroarenes with identical halogen atoms, highly selective monocoupling reactions have often been achieved only after a careful optimization of reaction parameters including the catalyst precursor, base, solvent, and the molar ratio between electrophile and organoboron reagent. This critical review with 341 references covers developments on the chemo-and site-selective Suzuki-Miyaura monocoupling reactions of polyhalogenated heteroarenes with different or identical halogen atoms. It also includes the synthesis of polysubstituted heteroarenes, not easily accessible by other means, via consecutive monocoupling reactions and/ or a more synthetically valuable approach involving one-pot polycoupling reactions.

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“…This approach has also been used to prepare substituted 2-pyranones (Scheme S5). 16 The starting compound S5-1 was reacted with arylboronic acids under distinct reaction conditions to accomplish the synthesis of the target molecules. In the first step, the bromine atom was substituted using Pd 2 (dba) 3 and (2-biphenyl)di-tertbutylphosphine (JohnPhos).…”

Section: Scheme S4 Stereoselective Synthesis Of Terminal Vinyl Monoflmentioning

confidence: 99%

Cross-Coupling Reactions of Double or Triple Electrophilic Templates for Alkene Synthesis

Edlová¹,

Čubiňák²,

Tobrman³

2020

Synthesis

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This short review summarizes the latest advances in the cross-coupling reactions of double and triple electrophilic templates bearing halogen atoms and an activated C–O bond. Reactions involving the formation of a C–C bond as part of di-, tri-, and tetrasubstituted double bond systems are highlighted.1 Introduction2 Cross-Coupling Reactions of Halovinyl Tosylates3 Cross-Coupling Reactions of Halovinyl Triflates4 Cross-Coupling Reactions of Halovinyl Phosphates5 Cross-Coupling Reactions of Halovinyl Esters6 Conclusion

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Generation of diverse 2-pyrones via palladium-catalyzed site-selective Suzuki-Miyaura couplings of 3-bromo-4-tosyloxy-2-pyrone

Abstract: Based on different reactivity of the (pseudo)halide substituents in the 2-pyrone (3-Br and 4-OTs), palladium-catalyzed sequential site-selective Suzuki-Miyaura cross-coupling reactions of 3-bromo-6-methyl-4-tosyloxy-2-pyrone are described, which afford the diverse 2-pyrones in good yields.

Cited by 18 publications

References 68 publications

Synthesis, C–H bond functionalisation and cycloadditions of 6-styryl-1,2-oxathiine 2,2-dioxides

Synthesis, C–H bond functionalisation and cycloadditions of 6-styryl-1,2-oxathiine 2,2-dioxides

Selective Palladium‐Catalyzed Suzuki–Miyaura Reactions of Polyhalogenated Heteroarenes

Cross-Coupling Reactions of Double or Triple Electrophilic Templates for Alkene Synthesis

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