92862-23-2Relevant academic research and scientific papers
A General Approach to Intermolecular Olefin Hydroacylation through Light-Induced HAT Initiation: An Efficient Synthesis of Long-Chain Aliphatic Ketones and Functionalized Fatty Acids
Guin, Joyram,Paul, Subhasis
supporting information, p. 4412 - 4419 (2021/02/05)
Herein, an operationally simple, environmentally benign and effective method for intermolecular radical hydroacylation of unactivated substrates by employing photo-induced hydrogen atom transfer (HAT) initiation is described. The use of commercially available and inexpensive photoinitiators (Ph2CO and NHPI) makes the process attractive. The olefin hydroacylation protocol applies to a wide array of substrates bearing numerous functional groups and many complex structural units. The reaction proves to be scalable (up to 5 g). Different functionalized fatty acids, petrochemicals and naturally occurring alkanes can be synthesized with this protocol. A radical chain mechanism is implicated in the process.
Mild and direct conversion of esters to morpholine amides using diisobutyl(morpholino)aluminum: Application to efficient one-pot synthesis of ketones and aldehydes from esters
Jeon, Ah Ram,Kim, Min Eai,Park, Jae Kyo,Shin, Won Kyu,An, Duk Keun
, p. 4420 - 4424 (2014/06/10)
Morpholine amide intermediates, which are easily prepared by aminolysis of various esters with diisobutyl(morpholino)aluminum, react with organolithium and reducing agents (DIBALH or LDBMA) without isolation of the aminolysis intermediates to give ketones in 83-95% yields and aldehydes quantitatively.
An effective one-pot conversion of acid chlorides to aldehydes and ketones
Park, Jae Kyo,Shin, Won Kyu,An, Duk Keun
, p. 3199 - 3203 (2013/06/27)
Aldehydes and ketones were synthesized from their respective acid chlorides via a one-pot protocol. Morpholine amide intermediates that were readily prepared by the aminolysis of various acid chlorides with diisobutyl(morpholino) aluminum smoothly reacted with the reducing agent LDBMA and the organolithium reagents under mild reaction conditions (0 C), giving almost excellent product yields of up to 95%.
Ruthenium-catalyzed isomerization of alkenol into alkanone in water under irradiation of microwaves
Ishibashi, Kenichi,Takahashi, Masaaki,Yokota, Yutaka,Oshima, Koichiro,Matsubara, Seijiro
, p. 664 - 665 (2007/10/03)
Ruthenium catalyzed isomerization of alkenol into alkanone through a migration of C-C double bond was performed in water under irradiation of microwaves. When the reaction was performed in deuterium oxide instead of water, the trail of the migration was shown by H-D exchange reaction. Copyright
Hydrogen transfer type oxidation of alcohols by rhodium and ruthenium catalyst under microwave irradiation
Takahashi, Masaaki,Oshima, Koichiro,Matsubara, Seijiro
, p. 9201 - 9204 (2007/10/03)
Secondary alcohols were converted into the corresponding ketones by methyl acrylate and rhodium catalyst efficiently under microwave irradiation. Treatment of primary alcohols with the same condition resulted in the recovery of the starting materials. Primary alcohols were converted into aldehydes by hydrogen transfer reaction using methyl vinyl ketone and ruthenium catalyst under microwave irradiation.
Chemoselective conversion of conjugated nitroalkenes into ketones by sodium borohydride-hydrogen peroxide: A new synthesis of 4-oxoalkanoic acids, dihydrojasmone and (±)exo-brevicomin
Ballini,Bosica
, p. 723 - 726 (2007/10/02)
A new, simple, cheap, and practical procedure for the direct transformation of α,β-unsaturated nitroalkenes into ketones has been realized by the NaBH4/H2O2 system. By this method, other functional groups such as C-C double bonds, ketals or aromatic nitro groups were preserved. Application of this methodology to the preparation of 4-oxoalkanoic acids, dihydrojasmone, and (±)-exobrevicomin is also reported.
Electrochemical Oxidation of Acylsilanes and Their Tosylhydrazones
Yoshida, Jun-ichi,Itoh, Masanori,Matsunaga, Shin-ichiro,Isoe, Sachihiko
, p. 4877 - 4882 (2007/10/02)
Oxidation potentials of acylsilanes were found to be much less positive than those of ketones and aldehydes.The effect of silicon is attributed to the rise of the HOMO level by the interaction between the C-Si ? orbital and the nonbonding p orbital of the carbonyl oxygen which in turn favors the electron transfer.Preparative electrochemical oxidation of acylsilanes proceeded smoothly, giving rise to facile cleavage of the C-Si bond and the introduction of nucleophiles such as alcohols, water, and carbamates onto the carbonyl carbon.Electrochemical properties of tosylhydrazones of acylsilanes were also investigated.A decrease in oxidation potential of tosylhydrazones caused by silyl substitution was found to be smaller than that for carbonyl compounds.Preparative electrochemical oxidation of tosylhydrazones of acylsilanes gave the corresponding nitriles with consumption of a catalytic amount of electricity.
