1352818-97-3Relevant academic research and scientific papers
Iterative Arylation of Amino Acids and Aliphatic Amines via δ-C(sp3)?H Activation: Experimental and Computational Exploration
Guin, Srimanta,Dolui, Pravas,Zhang, Xinglong,Paul, Satyadip,Singh, Vikas Kumar,Pradhan, Sukumar,Chandrashekar, Hediyala B.,Anjana,Paton, Robert S.,Maiti, Debabrata
, p. 5633 - 5638 (2019)
Directed C?H functionalization has been realized as a complementary tool to the traditional approaches for a straightforward access of non-proteinogenic amino acids; albeit such a process is restricted mostly up to the γ-position. In the present work, we demonstrate the diverse (hetero)arylation of amino acids and analogous aliphatic amines selectively at the remote δ-position by tuning the reactivity controlled by ligands. An organopalladium δ-C(sp3)?H activated intermediate has been isolated and crystallographically characterized. Mechanistic investigations carried out experimentally in conjunction with computational studies shed light on the difference in the mechanistic picture depending on the substrate structure.
Heterocycle synthesis via direct C-H/N-H coupling
Nadres, Enrico T.,Daugulis, Olafs
supporting information; experimental part, p. 7 - 10 (2012/02/16)
A method for five- and six-membered heterocycle formation by palladium-catalyzed C-H/N-H coupling is presented. The method employs a picolinamide directing group, PhI(OAc)2 oxidant, and toluene solvent at 80-120 °C. Cyclization is effective for sp2 as well as aliphatic and benzylic sp3 C-H bonds.
