37442-45-8Relevant articles and documents
Reevaluation of the mechanism of the Baylis-Hillman reaction: Implications for asymmetric catalysis
Aggarwal, Varinder K.,Fulford, Sarah Y.,Lloyd-Jones, Guy C.
, p. 1706 - 1708 (2005)
(Chemical Equation Presented) One step beyond: Proton transfer (step 3, see scheme), not C-C bond formation (step 2) as previously thought, is the rate-limiting step (RLS) in the initial stage of the Baylis-Hillman reaction, which involves the amine-catal
Can Heteroarenes/Arenes Be Hydrogenated Over Catalytic Pd/C Under Ambient Conditions?
Tanaka, Nao,Usuki, Toyonobu
supporting information, p. 5514 - 5522 (2020/07/24)
Hydrogenation of over a dozen aromatic compounds, including both heteroarenes and arenes, over palladium on carbon (Pd/C, 1–100 molpercent) with H2-balloon pressure at room temperature is reported. Analyses using pyridine as a model substrate revealed that acetic acid was the best solvent, as using only 1 molpercent Pd/C provided piperidine quantitatively. Substrate scope analysis and density functional theory calculations indicated that reaction rates are highly dependent on frontier molecular orbital characteristics and the steric bulkiness of substituents. Moreover, the established method was used for the concise synthesis of the anti-Alzheimer drug donepezil (Aricept?).
Enantioselective Lewis base catalyzed phosphonyldifluoromethylation of allylic fluorides using a: C -silyl latent pronucleophile
Zi, You,Lange, Markus,Vilotijevic, Ivan
supporting information, p. 5689 - 5692 (2020/06/19)
The first enantioselective phosphonyldifluoromethylation is enabled by the use of diethyl (difluoro(trimethylsilyl)-methyl)phosphonate reagent as a latent pronucleophile in the Lewis base catalyzed substitution of allylic fluorides. The reaction proceeds
Azidophosphonium salt-directed chemoselective synthesis of (E)/(Z)-cinnamyl-1H-Triazoles and regiospecific access to bromomethylcoumarins from Morita-Baylis-Hillman adducts
Karthikeyan, Soundararajan,Shobana, Radha Krishnan,Subimol, Kamarajapurathu Raju,Helen Ratna Monica,Kumar, Ayyanoth Karthik Krishna
, p. 1579 - 1587 (2020/09/16)
The direct transformation of Morita-Baylis-Hillman (MBH) adducts into molecules of interest is a crucial process wherein allylic hydroxy-protected or halogenated MBH adducts are commonly preferred. Herein, we report an azidophosphonium salt (AzPS)-catalys