Rate enhancement of the Morita–Baylis–Hillman reaction through mechanochemistry

Mack, James; Shumba, Maxwell

doi:10.1039/b612983h

Cited by 111 publications

(60 citation statements)

References 29 publications

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“…Mechanistically related is the Morita-Baylis-Hillman reaction, studied by Mack under ball milling conditions (Scheme 8). [204] Using dabco (20 mol%) as the catalyst, a major rate enhancement was observed, producing products in high yields after a short reaction time (30 min). Wittig olefination is important for the formation of alkenes.…”

Section: Stoichiometric Organic Reactions In Ball Millsmentioning

confidence: 99%

Mechanochemistry: opportunities for new and cleaner synthesis

et al. 2012

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Section: Stoichiometric Organic Reactions In Ball Millsmentioning

confidence: 99%

Mechanochemistry: opportunities for new and cleaner synthesis

et al. 2012

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“…9 The above mentioned High Speed Ball-Milling technique has been increasingly used in synthetic organic chemistry to promote several solvent-free reactions. Reported applications include: Heck-type cross-couplings, 10 Knoevenagel condensation reactions, 11 BayliseHillman reactions, 12 Michael additions, 11 functionalization of fullerenes, 13 synthesis of nitrones, 14 synthesis of peptides, 15 and others.…”

Section: Introductionmentioning

confidence: 99%

Efficient ball-mill procedure in the ‘green’ asymmetric aldol reaction organocatalyzed by (S)-proline-containing dipeptides in the presence of water

2011

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“…It is often reported that days or even weeks have been required for the reaction to complete. Therefore, a number of efforts have been made to accelerate Baylis-Hillman reaction, including use of Lewisacids, 2 ionic liquids, 3 and H-bond donors, 4 application of solvent-free, 5 high pressure, 6 ultrasound, 7 and microwave 8 techniques as well as development of highly active catalysts. 9 Most of these efforts were just successful for a limited number of substrates.…”

Section: Introductionmentioning

confidence: 99%