Chemistry:Homoenolates

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Homoenolates are a type of functional group that have been used in synthetic organic chemistry since the 1980s. They are related to enolates, but represent an umpolung of their reactivity. Homoenolates can be formed with a variety of different metal counterions, including lithium, iron, silver, lead, titanium, tin, tellurium, zirconium, niobium, mercury, zinc, antimony, bismuth, nickel, palladium, and copper. Homoenolates stability and reactivity varies by counterion identity and other nearby functional groups. Common pathways of decomposition include proto-demetalation and beta-hydride elimination. Multiple reviews on the topic of homoenolates and their reactivity have been published.[1][2][3][4][5][6]

Homoenolate polarity.png

References

  1. ↑ Hoppe, Dieter (1 December 1984). "The Homoaldol Reaction, or How to Overcome Problems of Regio- and Stereo-selectivity". Angewandte Chemie International Edition (Wiley) 23 (12): 932–948. doi:10.1002/anie.198409321. ISSN 0570-0833. 
  2. ↑ Isao, Kuwajima; Eiichi, Nakamura (1990). "Metal Homoenolates from Siloxycyclopropanes". Topics Curr Chem 155. https://www.uwindsor.ca/people/jgreen/sites/uwindsor.ca.people.jgreen/files/top-curr-chem-1990-155-1-kuwajima.pdf. 
  3. ↑ Crimmins, M. T.; Nantermet, P. G. (1993). "Homoenolates and Other Functionalized Organometallics. A Review". Organic Preparations and Procedures International 25: 41–81. doi:10.1080/00304949309457932. 
  4. ↑ Menon, R. S.; Biju, A. T.; Nair, V. (7 August 2015). "Recent Advances in Employing Homoenolates Generated by N-heterocyclic Carbene (NHC) Catalysis in Carbon-Carbon Bond-Forming Reactions". Chemical Society Reviews 44 (15): 5040–5052. doi:10.1039/c5cs00162e. PMID 26014054. 
  5. ↑ Nikolaev, A.; Orellana, A. (2016). "Transition-Metal-Catalyzed C–C and C–X Bond-Forming Reactions Using Cyclopropanols". Synthesis 48 (12): 1741–1768. doi:10.1055/s-0035-1560442. 
  6. ↑ Mills, L. R.; Rousseaux, S. A. L. (2019). "Modern Developments in the Chemistry of Homoenolates". European Journal of Organic Chemistry 2019: 6–26. doi:10.1002/ejoc.201801312. 




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