One-Pot Conversion of Aldehydes and Aryl Halides to Disubstituted Alkynes via Tandem Seyferth–Gilbert Homologation/Copper-Free Sonogashira Coupling

Sapegin, Alexander

doi:10.1021/acs.joc.9b01367

Cited by 8 publications

(3 citation statements)

References 44 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Conversion of aldehyde to terminal alkyne was accomplished via Seyferth-Gilbert Homologation. 19 To improve the reaction efficiency, we screened three bases including K 2 CO 3 , NaOMe and LDA/TMSCHN 2 , and found K 2 CO 3 /MeOH combination at room temperature could achieve a relatively high yield (Table 2). a All reactions were performed in DMF at 50 °C for 5 h. b Compound 3 1 eq., organozinc halides 2 eq.…”

Section: Resultsmentioning

confidence: 99%

Design and synthesis of a clickable, photoreactive amino acid p-(4-(but-3-yn-1-yl)benzoyl)-l-phenylalanine for peptide photoaffinity labeling

Han¹,

Wang²,

Bao³

et al. 2023

RSC Adv.

View full text Add to dashboard Cite

show abstract

Section: Resultsmentioning

confidence: 99%

Design and synthesis of a clickable, photoreactive amino acid p-(4-(but-3-yn-1-yl)benzoyl)-l-phenylalanine for peptide photoaffinity labeling

Han¹,

Wang²,

Bao³

et al. 2023

RSC Adv.

View full text Add to dashboard Cite

show abstract

“…A tandem Seyferth−Gilbert homologation/copper‐Free Sonogashira coupling was presented to afford disubstituted alkynes with one‐pot conversion from aldehydes and aryl halides using Pd/ XPhos catalyst system (Scheme 9c). [ 60 ]…”

Section: Classical Sonogashira Coupling Reactionsmentioning

confidence: 99%

Recent Expedition inPd‐CatalyzedSonogashira Coupling and Related Processes^†

2023

View full text Add to dashboard Cite

Sonogashira cross-coupling protocol, typically showing the reaction between aryl/vinyl halide and terminal alkyne, has been a widely used protocol for constructing C(sp 2 )-C(sp) bond. The resulting internal alkynes are highly versatile for reaching differently functionalized alkyne-containing scaffolds or serving as valuable synthetic synthons to many other functional groups. It is worth noting that products originated from this coupling reaction are mostly applicable to be transformed into corresponding Z-alkene, alkane, or heterocyclic moieties in natural product syntheses. The reaction conditions and catalyst systems are able to be tweaked in order to facilitate the activation of steric hindered and/or electron-rich electrophiles. Pd-catalyzed copper-free Sonogashira coupling reaction has caught increasing attention as the improved method can be more environmentally friendly. What is more, the conditions of the coupling reaction can be readily amended to allow the fusion of other carbonylation or decarboxylation step in the catalytic cycle, and thus allow more complex yet versatile convergent synthesis to proceed in an operationally simple one-pot manner.

show abstract

“…Our analysis bares similar trends to Kumada–Corriu and Negishi cross-coupling reactions in that there is a greater use (52% of the data) of lower mol % values. From the journal articles examined (44 articles and 55 reactions, Figure ), ,− almost a third of the reactions make use of 1–2 mol % Pd catalyst with 25% employing 1 mol % or lower. The Sonogashira reaction shows a trend toward lower ppm values, typically in the 500 ppm and lower region (median value of 360 ppm).…”

Section: Sonogashira Cross-couplingmentioning

confidence: 99%

Pd-Catalyzed Cross-Couplings: On the Importance of the Catalyst Quantity Descriptors, mol % and ppm

Horbaczewskyj

Fairlamb

2022

Org. Process Res. Dev.

View full text Add to dashboard Cite

This Review examines parts per million (ppm) palladium concentrations in catalytic cross-coupling reactions and their relationship with mole percentage (mol %). Most studies in catalytic cross-coupling chemistry have historically focused on the concentration ratio between (pre)catalyst and the limiting reagent (substrate), expressed as mol %. Several recent papers have outlined the use of “ppm level” palladium as an alternative means of describing catalytic cross-coupling reaction systems. This led us to delve deeper into the literature to assess whether “ppm level” palladium is a practically useful descriptor of catalyst quantities in palladium-catalyzed cross-coupling reactions. Indeed, we conjectured that many reactions could, unknowingly, have employed low “ppm levels” of palladium (pre)catalyst, and generally, what would the spread of ppm palladium look like across a selection of studies reported across the vast array of the cross-coupling chemistry literature. In a few selected examples, we have examined other metal catalyst systems for comparison with palladium.

show abstract

One-Pot Conversion of Aldehydes and Aryl Halides to Disubstituted Alkynes via Tandem Seyferth–Gilbert Homologation/Copper-Free Sonogashira Coupling

Cited by 8 publications

References 44 publications

Design and synthesis of a clickable, photoreactive amino acid p-(4-(but-3-yn-1-yl)benzoyl)-l-phenylalanine for peptide photoaffinity labeling

Design and synthesis of a clickable, photoreactive amino acid p-(4-(but-3-yn-1-yl)benzoyl)-l-phenylalanine for peptide photoaffinity labeling

Recent Expedition inPd‐CatalyzedSonogashira Coupling and Related Processes^†

Pd-Catalyzed Cross-Couplings: On the Importance of the Catalyst Quantity Descriptors, mol % and ppm

Contact Info

Product

Resources

About

One-Pot Conversion of Aldehydes and Aryl Halides to Disubstituted Alkynes via Tandem Seyferth–Gilbert Homologation/Copper-Free Sonogashira Coupling

Cited by 8 publications

References 44 publications

Design and synthesis of a clickable, photoreactive amino acid p-(4-(but-3-yn-1-yl)benzoyl)-l-phenylalanine for peptide photoaffinity labeling

Design and synthesis of a clickable, photoreactive amino acid p-(4-(but-3-yn-1-yl)benzoyl)-l-phenylalanine for peptide photoaffinity labeling

Recent Expedition inPd‐CatalyzedSonogashira Coupling and Related Processes†

Pd-Catalyzed Cross-Couplings: On the Importance of the Catalyst Quantity Descriptors, mol % and ppm

Contact Info

Product

Resources

About

Recent Expedition inPd‐CatalyzedSonogashira Coupling and Related Processes^†