72302-28-4Relevant academic research and scientific papers
Stereoselective arylation of substituted cyclopentenes by substrate-directable Heck-Matsuda reactions: A concise total synthesis of the sphingosine 1-phosphate receptor (S1P1) agonist VPC01091
Oliveira, Caio C.,Dos Santos, Emerson A. F.,Bormio Nunes, Julia H.,Correia, Carlos Roque D.
, p. 8182 - 8190,9 (2012)
We describe herein an efficient and diastereoselective substrate-directable Heck-Matsuda reaction with nonactivated five-membered olefins. The carbamate acts as the main directing group in the arylation process allowing the synthesis of several functionalized aryl cyclopentenes in good to excellent diastereoselectivities (>85:15) and in isolated yields ranging from 41 to 90%. No double bond isomerizations were observed in these Heck reactions, and the newly created benzylic centers were preserved in all cases examined. The substrate directable Heck arylation approach was successfully applied in a straightforward total synthesis of the sphingosine 1-phosphate receptor-subtype 1 (S1P1) agonist VPC01091 by a concise and practical route involving 5 steps in 40% overall yield.
Covalent modification of iron surfaces by electrochemical reduction of aryldiazonium salts
Adenier,Bernard,Chehimi,Cabet-Deliry,Desbat,Fagebaume,Pinson,Podvorica
, p. 4541 - 4549 (2001)
Electrochemical reduction of aryldiazonium salts (in acetonitrile or acidic aqueous medium) on an iron or mild steel surface permits the strong bonding (which resists an ultrasonic cleaning) of aryl groups on these surfaces. Attachment of aryl groups was
Crown Cation Complex Effects. 12. Dissolution and Complexation of Arenediazonium Cations in Nonpolar Media. An Assessment of Solvent Effects and Reactivity by Infrared and Nuclear Magnetic Resonance Spectroscopy
Korzeniowski, Stephen H.,Leopold, Ahuva,Beadle, James R.,Ahern, Michael F.,Sheppard, William A.,et al.
, p. 2153 - 2159 (2007/10/02)
A number of arenediazonium salts (largely tetrafluoroborates) have been surveyed to determine their solubility properties and the influence of crown ethers and quaternary ammonium salts thereupon.Analysis has been by a variety of spectral techniques inclu
