2040-26-8Relevant articles and documents
Reaction of selenoketones with propiolic acid
Okuma, Kentaro,Koda, Masahiro,Shigetomi, Toshiyuki
, p. 1057 - 1060 (2008)
The reaction of di-tert-butyl selenoketone with propiolic acid gave 2H,6H-1,3-oxaselenin-6-one in 78% yield, whereas the reaction of di-tert-butyl thioketone with propiolic acid recovered starting thioketone almost quantitatively. On the other hand, the r
Palladium-NHC (NHC = N-heterocyclic Carbene)-Catalyzed Suzuki-Miyaura Cross-Coupling of Alkyl Amides
Wang, Chang-An,Rahman, Md. Mahbubur,Bisz, Elwira,Dziuk, B?az?ej,Szostak, Roman,Szostak, Michal
, p. 2426 - 2433 (2022/02/17)
We report the Pd-catalyzed Suzuki-Miyaura cross-coupling of aliphatic amides. Although tremendous advances have been made in the cross-coupling of aromatic amides, C-C bond formation from aliphatic amides by selective N-C(O) cleavage has remained a major challenge. This longstanding problem in Pd catalysis has been addressed herein by a combination of (1) the discovery of N,N-pym/Boc amides as a class of readily accessible amide-based reagents for cross-coupling and (2) steric tuning of well-defined Pd(II)-NHC catalysts for cross-coupling. The methodology is effective for the cross-coupling of an array of 3°, 2°, and 1° aliphatic amide derivatives. The catalyst system is user-friendly, since the catalysts are readily available and are air- and bench-stable. Mechanistic studies strongly support an amide bond twist and external nN → π*C═O/Ar delocalization as a unified enabling feature of N,N-pym/Boc amides in selective N-C(O) bond activation. The method provides a rare example of Pd-NHC-catalyzed cross-coupling of aliphatic acyl amide electrophiles.
1,3-Alkyl Transposition in Allylic Alcohols Enabled by Proton-Coupled Electron Transfer
Knowles, Robert R.,Seidler, Gesa,Zhao, Kuo
supporting information, p. 20190 - 20195 (2021/08/13)
A method is described for the isomerization of acyclic allylic alcohols into β-functionalized ketones via 1,3-alkyl transposition. This reaction proceeds via light-driven proton-coupled electron transfer (PCET) activation of the O?H bond in the allylic al
Electrochemical [4+2] Annulation-Rearrangement-Aromatization of Styrenes: Synthesis of Naphthalene Derivatives
Ma, Yueyue,Lv, Jufeng,Liu, Chengyu,Yao, Xiantong,Yan, Guoming,Yu, Wei,Ye, Jinxing
supporting information, p. 6756 - 6760 (2019/04/17)
We report the first electrochemical strategy to synthesize functionalized naphthalene derivatives through [4+2] annulation—rearrangement–aromatization from styrenes under mild conditions. The electrolysis does not require metals, oxidants and high valence substrates, indicating the atom and step-economy ideals. The dehydrodimer produced through [4+2] cycloaddition of 4-methoxy α-methyl styrene is isolated and proved to be the key intermediate for the following oxydehydrogenation to form carbon cation, which undergoes rearrangement–aromatization to afford the final products. This reaction represents a powerful access to construct multi-substituted naphthalene blocks in a single step.