22023-25-2Relevant academic research and scientific papers
Cu(OTf)2-DBN/DBU complex as an efficient catalyst for allylic oxidation of olefins with tert-butyl perbenzoate
Sekar, Govindasamy,DattaGupta, Arpita,Singh, Vinod K.
, p. 8435 - 8436 (1996)
Olefins, on treatment with tert-butyl perbenzoate in the presence of a catalytic amount of a complex of Cu(OTf)2 and chelating ligands such as DBN and DBU gave allylic benzoates under milder conditions. A variety of olefins were tested in the reaction.
Water-soluble and reusable copper catalyst for the allylic benzoyloxylation of olefins
Le Bras, Jean,Muzart, Jacques
, p. 431 - 433 (2002)
Simple mixing of [(HOCH2CH2NHCOCH2)2NCH 2]2 with Cu(MeCN)4BF4 in water led to an efficient and reusable catalytic system for the allylic oxidation of olefins by tert-b
NHPI- and TBAI-Co-Catalyzed Synthesis of Allylic Esters from Toluene Derivatives and Alkenes
Li, Chengliang,Deng, Hongmei,Jin, Tao,Li, Chunju,Jia, Xueshun,Li, Jian
supporting information, p. 840 - 844 (2018/01/27)
An N -hydroxyphthalimide (NHPI) and tetrabutylammonium iodide (TBAI) co-catalyzed oxidative coupling reaction of toluene derivatives and alkenes has been disclosed. This method can serve as a new strategy to access allylic ester using toluene derivatives as oxyacylating reagent. This metal-free protocol also features the readily available starting materials, broad substrate scope, and mild reaction conditions.
Copper-catalyzed regioselective allylic oxidation of olefins via C–H activation
Zhu, Nengbo,Qian, Bo,Xiong, Haigen,Bao, Hongli
supporting information, p. 4125 - 4128 (2017/09/29)
A regioselective oxidation of allylic C–H bond to C–O bond catalyzed by copper (I) was developed with diacyl peroxides as oxidants. The oxidation of allylic C–H bond was accomplished with good yield and regioselectivity under mild reaction conditions. This method has a broad substrate scope including cyclic olefins, terminal and internal acyclic olefins and allyl benzene compounds. The reaction proceeds by a radical mechanism as suggested by spin trapping experiments.
Oxidation-Reduction Condensation of Diazaphosphites for Carbon-Heteroatom Bond Formation Based on Mitsunobu Mechanism
Huang, Hai,Kang, Jun Yong
supporting information, p. 544 - 547 (2017/02/10)
An efficient oxidation-reduction condensation reaction of diazaphosphites with various nonacidic pronucleophiles in the presence of DIAD as a weak oxidant has been developed for carbon-heteroatom bond formation. This mild process affords structurally diverse tertiary amines, secondary amines, esters, ethers, and thioethers in moderate to excellent yields. The selective synthesis of secondary amines from primary amines has been achieved. Importantly, a practical application to the synthesis of antiparkinsonian agent piribedil has been demonstrated.
Metal-free, one-pot synthesis of allylic and benzylic esters via decarboxylation and C-H bond activation
Mo, Hanjie,Chen, Dingben,Xu, Lingzhen,Chen, Di,Pan, Fuyou,Yang, Jianguo
supporting information, p. 209 - 215 (2015/05/05)
A tetrabutylammonium iodide catalyzed method has been developed for the one-pot synthesis of allylic and benzylic esters from α-oxo carboxylic acids and alkenes/alkylbenzenes via decarboxylation and C-H bond activation. Various allylic and benzylic esters were obtained in good yield.
Copper-catalyzed benzylic oxidation of C(sp3)-H bonds
Zhang, Bo,Zhu, Shou-Fei,Zhou, Qi-Lin
supporting information, p. 2033 - 2037 (2013/03/13)
A selective oxidation of benzylic C(sp3)-H bonds to C(sp 3)-O bonds catalyzed by copper complexes of quinoline-imine ligands was developed with peresters as oxidants under mild reaction conditions, which converted benzylic methylenes directly into benzylic alcohols and esters by means of direct C-H bond functionalization.
A chiral sulfoxide-ligated ruthenium complex for asymmetric catalysis: Enantio- and regioselective allylic substitution
Trost, Barry M.,Rao, Meera,Dieskau, Andre P.
supporting information, p. 18697 - 18704 (2014/01/06)
The design and synthesis of a novel chiral sulfoxide-ligated cyclopentadienyl ruthenium complex is described. Its utility as an asymmetric variant of [CpRu(MeCN)3]PF6 is demonstrated through its ability to function in the branched-selective asymmetric allylic alkylation of phenols and carboxylic acids. Water has also been shown to act as a competent nucleophile in this reaction to generate branched allyl alcohols with good regio- and enantioselectivities.
A convenient and versatile method for the preparation of α-hydroxymethyl ketone derivatives from the corresponding allyl silyl ethers or allyl carboxylates
Hon, Yung-Son,Wong, Ying-Chieh,Wu, Kuo-Jui
experimental part, p. 896 - 914 (2009/12/06)
The ozonolysis of 1-substituted allyl silyl ethers or 1-substituted allyl carboxylates followed by treatment with bases gave the corresponding α-silyloxymethyl- or α-acyloxymethyl-ketones in good yields. It is proposed to proceed via the corresponding α-silyloxy- or α-acyloxyaldehydes intermediates followed by 1,4-group migration. The results of theoretical calculations are applicable to explain the experimental results.
[(NHC)Au1]-catalyzed rearrangement of allylic acetates
Marion, Nicolas,Gealageas, Ronan,Nolan, Steven P.
, p. 2653 - 2656 (2008/02/09)
Equation Presented [(NHC)AuCl] complexes (NHC = N-heterocyclic carbene), in conjunction with a silver salt, were found to efficiently catalyze the rearrangement of allylic acetates under both conventional and microwave-assisted heating. The optimization of several reaction parameters (solvent, silver salt, and ligand) as well as a study of the reaction scope are reported. The steric hindrance of the ligand bound to gold was found crucial for the outcome of the reaction as only extremely bulky ligands permitted the isomerization.
