35840-83-6Relevant academic research and scientific papers
Palladium-Catalyzed Regioselective C-H Iodination of Unactivated Alkenes
Schreib, Benedikt S.,Carreira, Erick M.
supporting information, p. 8758 - 8763 (2019/06/13)
A palladium-catalyzed C-H iodination of unactivated alkenes is reported. A picolinamide directing group enables the regioselective functionalization of a wide array of olefins to furnish iodination products as single stereoisomers. Mechanistic investigations suggest the reversible formation of a six-membered alkenyl palladacycle intermediate through a turnover-limiting C-H activation.
Convenient route to primary (Z)-allyl amines and homologs
Gerpe, Alejandra,Bollini, Mariela,Gonzalez, Mercedes,Cerecetto, Hugo
experimental part, p. 29 - 47 (2009/04/06)
A convenient two-step procedure for the synthesis of primary (Z)-allyl amines, (Z)-homoallyl amines [(Z)-but-3-enylamines], and (Z)-pent-4-enylamines using the Wittig reaction was achieved. The use of nonstabilized ylides from triphenylphosphonium salt, potassium salt, and apolar solvent produced (Z/E)-geometric isomer ratios generally greater than 1.6. The amine moiety was masked using a phtalimide group that was removed successfully in the last step of the process in two different conditions, NH2NH2/EtOH/rt or CH3NH2/EtOH/rt. However, in some cases, reduction of the C = C double bond in the deprotection with hydrazine was concomitantly observed. Copyright Taylor & Francis Group, LLC.
Bronsted acid-catalyzed intramolecular hydroamination of protected alkenylamines. Synthesis of pyrrolidines and piperidines.
Schlummer, Bjoern,Hartwig, John F
, p. 1471 - 1474 (2007/10/03)
[reaction: see text]. The cyclization of aminoalkenes bearing an electron-withdrawing group on the nitrogen atom was catalyzed by triflic or sulfuric acid in toluene. Pyrrolidines and piperidines were formed in excellent yields. N-phenylanilides also underwent cyclization to form gamma-lactams.
Stereospecific synthesis of Z olefins bearing an ω-azido group.
Chhen, A.,Vaultier, M.,Carrie, R.
, p. 4953 - 4956 (2007/10/02)
Ylides derived from ω-azidoalkyltriphenylphosphonium salts were generated at low temperature.They are stable at -80 deg C for several hours and react smoothly and stereospecifically with typical aldehydes to form Z-ω-azido olefins which are the precursors of ω-unsaturated primary and secondary amines.
