81428-81-1Relevant articles and documents
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 oxidative decarbonylative Heck-type coupling of aromatic aldehydes with terminal alkenes
Kang, Lei,Zhang, Feng,Ding, Lin-Ting,Yang, Luo
, p. 100452 - 100456 (2015/12/09)
A rhodium-catalyzed oxidative decarbonylative Heck-type coupling of aromatic aldehydes with terminal alkenes to afford 1,2-disubstituted alkenes with good regio- and E-selectivity is developed. This reaction employs readily available aromatic aldehydes as the aryl electrophile counterpart and relies on selected acyl chloride as the crucial additive to activate the rhodium catalyst precursor.
Z-E photoisomerization of benzylidenebenzocyclobutenones via ketene- allene intermediates. A laser flash photolysis study
Boch,Bradley,Durst,Scaiano
, p. 19 - 22 (2007/10/02)
Benzylidenebenzocyclobutenones I-E and I-Z undergo photoinduced isomerization via the intermediacy of ketene-allene II which in acetonitrile has a lifetime of ~26 μs and can be trapped with water and methanol. Trapping by the latter occurs with a rate constant of 1.2 x 104 M-1 s-1 and leads to the expected ester. In addition to Z = E isomerization, product studies reveal the formation of dimeric products in very low quantum yields.
