396717-20-7Relevant articles and documents
Weak coordinated nitrogen functionality enabled regioselective C-H alkynylationviaPd(ii)/mono-N-protected amino acid catalysis
Liu, Bifu,Ouyang, Wensen,Nie, Jianhong,Gao, Yang,Feng, Kejun,Huo, Yanping,Chen, Qian,Li, Xianwei
, p. 11255 - 11258 (2020/10/06)
The exploration of weak coordinated amine derivative enabled regioselective C-H functionalization remains challenging due to the elusive achievement of reactivity and selectivity simultaneously. Herein, regioselective C-H alkynylation of various readily transformable nitrogen functionalities was developed with great efficiency, with the assistance of the mono-N-protected amino acid (MPAA) ligandviaPd(ii) catalysis proceedingvia5, 6 and 7-membered palladacycle intermediates.
Nickel-catalyzed direct alkynylation of C(sp2)-H bonds of amides: An "inverse Sonogashira strategy" to ortho-alkynylbenzoic acids
Landge, Vinod G.,Shewale, Chinmay H.,Jaiswal, Garima,Sahoo, Manoj K.,Midya, Siba P.,Balaraman, Ekambaram
, p. 1946 - 1951 (2016/04/05)
Nickel-catalyzed direct alkynylation of C(sp2)-H bonds of amides using commercially available, inexpensive 8-aminoquinoline as a removable bidentate directing group is described. The present ortho-alkynylation has a broad substrate scope, funct
Photochemical C2-C6 cyclization of enyne-allenes: Detection of a fulvene triplet diradical in the laser flash photolysis
Bucher, Goetz,Mahajan, Atul A.,Schmittel, Michael
supporting information; experimental part, p. 8815 - 8828 (2009/04/11)
(Chemical Equation Presented) A series of enyne-allenes, with and without benzannulation at the ene moiety and equipped with aromatic and carbonyl groups as internal triplet sensitizer units at the allene terminus, was synthesized. Both sets, the cyclohexenyne-allenes and benzenyne-allenes, underwent thermal C2-C6 cyclization exclusively to formal ene products. In contrast, the photochemical C2-C6 cyclization of enyne-allenes provided formal Diels-Alder and/or ene products, with higher yields for the benzannulated systems. A raise of the temperature in the photochemical cyclization of enyne-allene 1b′ led to increasing amounts of the ene product in relation to that of the formal Diels-Alder product. Laser flash photolysis at 266 and 355 nm as well as triplet quenching studies for 1b,b′ indicated that the C2-C6 cyclization proceeds via the triplet manifold. On the basis of a density functional theory (DFT) study, a short-lived transient (r = 30 ns) was assigned as a triplet allene, while a long-lived transient (τ = 33 μs) insensitive to oxygen was assigned as fulvene triplet diradical. An elucidation of the reaction mechanism using extensive DFT computations allowed rationalization of the experimental product ratio and its temperature dependence.
