89044-48-4Relevant articles and documents
Nickel-Catalyzed Domino Heck-Type Reactions Using Methyl Esters as Cross-Coupling Electrophiles
Zheng, Yan-Long,Newman, Stephen G.
, p. 18159 - 18164 (2019/11/13)
While esters are frequently used as traditional electrophiles in substitution chemistry, their application in cross-coupling chemistry is still in its infancy. This work demonstrates that methyl esters can be used as coupling electrophiles in Ni-catalyzed Heck-type reactions through the challenging cleavage of the C(acyl)?O bond under relatively mild reaction conditions at either 80 or 100 °C. With the σ-NiII intermediate generated from the insertion of acyl NiII species into the tethered C=C bond, carbonyl-retentive products were formed by domino Heck/Suzuki–Miyaura coupling and Heck/reduction pathways when organoboron and mild hydride nucleophiles are used.
Rh-catalyzed reagent-free ring expansion of cyclobutenones and benzocyclobutenones
Chen, Peng-Hao,Sieber, Joshua,Senanayake, Chris H.,Dong, Guangbin
, p. 5440 - 5445 (2015/09/28)
Here we report a reagent-free rhodium-catalyzed ring-expansion reaction via C-C cleavage of cyclobutenones. A variety of poly-substituted cyclopentenones and 1-indanones can be synthesized from simple cyclobutenones and benzocyclobutenones. The reaction condition is near pH neutral without additional oxidants or reductants. The potential for developing a dynamic kinetic asymmetric transformation of this reaction has also been demonstrated. Further study supports the proposed pathway involving Rh-insertion into the cyclobutenone C-C bond, followed by β-hydrogen elimination, olefin insertion and reductive elimination.
Carbon-13 Nuclear Magnetic Resonance Spectra of Pterosin-Sesquiterpenes and Related Indan-1-one Derivatives
Fukuoka, Masamichi,Yoshihira, Kunitoshi,Natori, Shinsaku,Mihashi, Kunihide,Nishi, Masatoshi
, p. 3113 - 3128 (2007/10/02)
Methyl derivatives of indan-1-one were prepared as models to aid in interpreting the carbon-13 nuclear magnetic resonance ((13)C-NMR) spectra of pterosin-sesquiterpenes which were isolated from bracken fern, Pteridium aquilinum var. latiusculum.The chemical shifts of the carbons of the methylindan-1-ones were assigned by the proton decoupling technique.All the (13)C-NMR signals of the pterosin-sesquiterpenes were assigned by means of selective proton decouplings, and from the (13)C-(1)H long-range couplings and (13)C chemical shifts of the model compounds.Keywords - indan-1-one derivative; methylindan-1-one; pterosin-sesquiterpene; methylindan-1-one synthesis; (1)H-NMR; (13)C-NMR; selective decoupling; C-H decoupling