396717-17-2Relevant articles and documents
A Mild and Regioselective Synthesis of α-Fluoroketones via Gold and Selectfluor Partnership
Chen, Xi,Martini, Sophie,Michelet, Véronique
, p. 3612 - 3618 (2019/07/10)
An efficient, mild and rapid synthesis of α-fluoroketones has been developed, via a fruitful association between gold and Selectfluor starting from aldehyde-yne and alkynylaryl ketone derivatives. Several functionalized and synthetically highly valuable α-fluoroketones (21 compounds, up to 92%) were isolated in good to excellent yields via a remarkable regioselective oxyfluorination reaction in EtOH/H2O at room temperature. We have shed some light on parts of the mechanism by reacting diphenylacetylene and aldehyde-yne with or without Selectfluor. The reaction most presumably occurs via a sequential gold-catalyzed regioselective hydration followed by the α-fluorination reaction, but the presence of aldehyde moiety is crucial for the reactivity of alkyne function. The fluoroketones were efficiently transformed to 4-fluoroisoquinolines (9 compounds, 82–95%) of high pharmaceutical interest. (Figure presented.).
Gold(I)-catalyzed cycloisomerizations and alkoxycyclizations of ortho-(alkynyl)styrenes
Sanjun, Ana M.,Rashid, Muhammad A.,Garca-Garca, Patricia,Martnez-Cuezva, Alberto,Fernndez-Rodrguez, Manuel A.,Rodrguez, Flix,Sanz, Roberto
supporting information, p. 3042 - 3052 (2015/02/05)
Indenes and related polycyclic structures have been efficiently synthesized by gold(I)-catalyzed cycloisomerizations of appropriate ortho-(alkynyl)styrenes. Disubstitution at the terminal position of the olefin was demonstrated to be essential to obtain products originating from a formal 5-endo-dig cyclization. Interestingly, a complete switch in the selectivity of the cyclization of o-(alkynyl)-a-methylstyrenes from 6-endo to 5-endo was observed by adding an alcohol to the reaction media. This allowed the synthesis of interesting indenes bearing an all-carbon quaternary center at C1. Moreover, dihydrobenzo[a]fluorenes can be obtained from substrates bearing a secondary alkyl group at the β-position of the styrene moiety by a tandem cycloisomerization/1,2-hydride migration process. In addition, diverse polycyclic compounds were obtained by an intramolecular gold-catalyzed alkoxycyclization of o-(alkynyl)styrenes bearing a nucleophile in their structure. Finally, the use of a chiral gold complex allowed access to elusive chiral 1H-indenes in good enantioselectivities.
On water: Silver-catalyzed domino approach for the synthesis of benzoxazine/oxazine-fused isoquinolines and naphthyridines from o-alkynyl aldehydes
Verma, Akhilesh K.,Choudhary, Deepak,Saunthwal, Rakesh K.,Rustagi, Vineeta,Patel, Monika,Tiwari, Rakesh K.
, p. 6657 - 6669 (2013/07/26)
An operationally simple domino approach for the silver-catalyzed synthesis of oxazine/benzoxazine-fused isoquinolines 5a-q and naphthyridines 6a-v by the reaction of o-alkynyl aldehydes 3a-aa with amines having embedded nucleophiles 4a-d under mild reacti
