173948-30-6Relevant articles and documents
Palladium-Catalyzed Allylic Amination of Allylic Alcohols with Tin(II) Chloride and Triethylamine
Masuyama, Yoshiro,Kagawa, Masaaki,Kurusu, Yasuhiko
, p. 1121 - 1122 (1995)
Allylic alcohols caused allylic amination with primary or secondary amines in the presence of a catalytic amount of Pd(PPh3)4 and stoichiometric amount of tin(II) chloride in THF at 50 deg C to produce the corresponding allylic amines regioselectively.
Practical regio- and stereoselective azidation and amination of terminal alkenes
Ojo, Olatunji S.,Miranda, Octavio,Baumgardner, Kyle C.,Bugarin, Alejandro
supporting information, p. 9354 - 9358 (2019/01/03)
There is significant interest in developing more rapid and efficient production of nitrogen-containing allylic compounds, as widely used in various syntheses. This work reports a variety of allylic azides and allylic amines synthesized by an efficient, new one-pot protocol that employs readily available terminal alkenes as starting materials. This method is highly regio- and stereoselective, affording the linear (E)-isomer, under metal-free conditions. This process tolerates several functional groups including halogen-containing molecules; it is general for azides and amine nucleophiles; and, adducts were obtained in good yields.
Anti-Markovnikov rearrangement in sulfur mediated allylic C-H amination of olefins
Zhang, Zhong,Du, Hongguang,Xu, Jiaxi,Li, Pingfan
supporting information, p. 11547 - 11550 (2016/10/03)
Cationic rearrangement reactions usually follow Markovnikov's rule to give more substituted carbocations as stable intermediates. During our study on sulfur mediated allylic C-H amination of olefins, very rare cases of anti-Markovnikov rearrangement from secondary carbocations toward primary carbocations or primary triflates were observed.