137919-07-4Relevant academic research and scientific papers
Copper porphyrin as efficient catalysts for esterification of allyl sp3 C–H bond with carboxylic acid
Xiong, Ming-Feng,Ali, Atif,Akram, Waseem,Zhang, Hao,Si, Li-Ping,Liu, Hai-Yang
, p. 93 - 97 (2019/04/08)
We described that copper 5,10,15,20-tetrakis (ethoxycarbonyl)porphyrin (TECP) catalyzed oxidative cross dehydrogenative coupling of allyl sp3 C–H bond with acid for the synthesis of allyl esters in a homogeneous system. This reaction proceeded
Copper-catalyzed oxidative coupling of acids with alkanes involving dehydrogenation: Facile access to allylic esters and alkylalkenes
Wang, Cheng-Yong,Song, Ren-Jie,Wei, Wen-Ting,Fan, Jian-Hong,Li, Jin-Heng
supporting information, p. 2361 - 2363 (2015/02/05)
We here describe a new copper-catalyzed oxidative coupling of acids with alkanes for the selective synthesis of allylic esters and alkylalkenes. This method achieves multiple dehydrogenation and esterification, representing a new unactivated C(sp3/s
Allylic oxidation of alkenes catalyzed by a copper-aluminum mixed oxide
Garcia-Cabeza, Ana Leticia,Marin-Barrios, Ruben,Moreno-Dorado, F. Javier,Ortega, Maria J.,Massanet, Guillermo M.,Guerra, Francisco M.
supporting information, p. 1598 - 1601 (2014/04/17)
A strategy for the allylic oxidation of cyclic alkenes with a copper-aluminum mixed oxide as catalyst is presented. The reaction involves the treatment of an alkene with a carboxylic acid employing tert-butyl hydroperoxide as the oxidant. In all cases, the corresponding allylic esters are obtained. When l-proline is employed, the allylic alcohol or ketone is obtained. The oxidation of cyclohexene and valencene has been optimized by design of experiments (DoE) statistical methodology.
The Influence of Remote Heteroatom Substituents on the Stereoselectivity of Cyclopentene Ozonolysis
Bunnelle, William H.,Isbell, Terry A.
, p. 729 - 740 (2007/10/02)
The stereoselectivity for ozonide formation from cyclopentenes with allylic heteroatom substituents has been examined.Silyl ethers give high selectivity in favor of the exo-substituted ozonide, while esters of 2-cyclopentenol form ozonide mixtures with little stereoselection.Trapping experiments establish that fragmentation of the primary ozonides is highly regioselective to give only one of the isomeric ω-oxo carbonyl oxide intermediates and that the variation in final ozonide stereochemistry results from differing interactions between the remote substituent groupsand the carbonyl oxide system during cyclization of this intermediate.The effect of substituent and solvent on ozonide stereochemistry suggests a dominant role for electrostatic repulsion between carbonyl oxide and the heteroatom substituent during intramolecular cycloaddition.A chair-like transition state is proposed for this process and is in accord with the increase in exo selectivity for derivatives of 2-methyl-2-cyclopentenol.
