158987-25-8Relevant academic research and scientific papers
Achiral Pyridine Ligand-Enabled Enantioselective Radical Oxytrifluoromethylation of Alkenes with Alcohols
Cheng, Yong-Feng,Dong, Xiao-Yang,Gu, Qiang-Shuai,Yu, Zhang-Long,Liu, Xin-Yuan
, p. 8883 - 8886 (2017)
A conceptually novel strategy with achiral pyridine as the ancillary ligand to stabilize high-valent copper species for the first asymmetric radical oxytrifluoromethylation of alkenes with alcohols under CuI/phosphoric acid dual-catalysis has been developed. The transformation features mild reaction conditions, a remarkably broad substrate scope and excellent functional group tolerance, offering an efficient approach to a wide range of trifluoromethyl-substituted tetrahydrofurans bearing an α-tertiary stereocenter with excellent enantioselectivity. Mechanistic studies support the presumed role of the achiral pyridine as a coordinative ligand on copper metal to stabilize the key transient reaction species involved in the asymmetric induction process.
Copper-Catalyzed Modular Amino Oxygenation of Alkenes: Access to Diverse 1,2-Amino Oxygen-Containing Skeletons
Hemric, Brett N.,Chen, Andy W.,Wang, Qiu
supporting information, p. 1468 - 1488 (2019/01/25)
Copper-catalyzed alkene amino oxygenation reactions using O-acylhydroxylamines have been achieved for a rapid and modular access to diverse 1,2-amino oxygen-containing molecules. This transformation is applicable to the use of alcohols, carbonyls, oximes, and thio-carboxylic acids as nucleophiles on both terminal and internal alkenes. Mild reaction conditions tolerate a wide range of functional groups, including ether, ester, amide, carbamate, and halide. The reaction protocol allows for starting with free amines as the precursor of O-benzoylhydroxylamines to eliminate their isolation and purification, contributing to broader synthetic utilities. Mechanistic investigations reveal the amino oxygenation reactions may involve distinct pathways, depending on different oxygen nucleophiles.
Rhodium-Catalyzed Cyclization of O,ω-Unsaturated Alkoxyamines: Formation of Oxygen-Containing Heterocycles
Escudero, Julien,Bellosta, Véronique,Cossy, Janine
supporting information, p. 574 - 578 (2018/02/21)
O,ω-Unsaturated N-tosyl alkoxyamines undergo unexpected RhIII-catalyzed intramolecular cyclization by oxyamination to produce oxygen-containing heterocycles. Mechanistic studies show that an aziridine intermediate seems to be responsible for the formation of the heterocycles, possibly via a RhV species.
Interfacial electric field effects on a carbene reaction catalyzed by Rh porphyrins
Gorin, Craig F.,Beh, Eugene S.,Bui, Quan M.,Dick, Graham R.,Kanan, Matthew W.
, p. 11257 - 11265 (2013/08/23)
An intramolecular reaction catalyzed by Rh porphyrins was studied in the presence of interfacial electric fields. 1-Diazo-3,3-dimethyl-5-phenylhex-5-en- 2-one (2) reacts with Rh porphyrins via a putative carbenoid intermediate to form cyclopropanation pro
