103859-86-5Relevant articles and documents
Catalytic Intermolecular Carboamination of Unactivated Alkenes via Directed Aminopalladation
Liu, Zhen,Wang, Yanyan,Wang, Zichen,Zeng, Tian,Liu, Peng,Engle, Keary M.
, p. 11261 - 11270 (2017)
An intermolecular 1,2-carboamination of unactivated alkenes proceeding via a Pd(II)/Pd(IV) catalytic cycle has been developed. To realize this transformation, a cleavable bidentate directing group is used to control the regioselectivity of aminopalladation and stabilize the resulting organopalladium(II) intermediate, such that oxidative addition to a carbon electrophile outcompetes potential β-hydride elimination. Under the optimized reaction conditions, a broad range of nitrogen nucleophiles and carbon electrophiles are compatible coupling partners in this reaction, affording moderate to high yields. The products of this reaction can be easily converted to free ?3-amino acids and ?3-lactams, both of which are common structural motifs found in drug molecules and bioactive compounds. Reaction kinetics and DFT calculations shed light on the mechanism of the reaction and explain empirically observed reactivity trends.
From paracetamol to rolipram and derivatives: Application of deacetylation-diazotation sequences and palladium-catalyzed matsuda-heck reaction
Schmidt, Bernd,Elizarov, Nelli,Berger, Rene,Petersen, Monibh.
, p. 1174 - 1180 (2013/06/05)
A six-step synthesis of the antidepressant rolipram from the popular analgetic 4-acetamidophenol (paracetamol) is described. The steps include oxidative functionalization of the aromatic core, diazonium salt formation via deacetylation-diazotation, Matsuda-Heck reaction, conjugate addition of nitromethane, and hydrogenative cyclization. Georg Thieme Verlag Stuttgart · New York.