91496-96-7Relevant academic research and scientific papers
Gallium-Catalyzed Scriabine Reaction
Pareek, Manish,Bour, Christophe,Gandon, Vincent
supporting information, p. 6957 - 6960 (2018/11/21)
γ-Aryl enol acetates are easily obtained from diacetoxy alkenes and electron-rich arenes at room temperature using GaCl3 as catalyst. The products can then be converted into β-aryl aldehydes. This method represents the first broadly applicable catalytic version of the Scriabine reaction. DFT computations shed light on the mechanism of this transformation.
S,O-ligand-promoted palladium-catalyzed C–H olefination of arenes with allylic substrates
Naksomboon, Kananat,álvarez-Casao, Yolanda,Uiterweerd, Michiel,Westerveld, Nick,Maciá, Beatriz,Fernández-Ibá?ez, M. ángeles
supporting information, p. 379 - 382 (2017/12/28)
An efficient catalytic system for the C–H olefination of arenes with different allylic substrates is reported. The catalytic system is based on Pd(OAc)2 and a readily accessible bidentate S,O-ligand. The methodology shows high activity with a wide range of arenes, including bulky and, electron-rich and -poor arenes. The applicability of this catalyst is demonstrated in the late-stage functionalization of the complex molecule O-methylestrone.
Control of chemo-, regio-, and stereoselectivities in ligand-free Pd-catalyzed oxidative heck reactions of arylboronic acids or alkenylboronate with allyl esters
Su, Yijin,Jiao, Ning
supporting information; experimental part, p. 2980 - 2983 (2009/12/05)
A ligand-free Pd-catalyzed highly selective oxidative Heck reaction of organoboronic acids with allyl esters was developed. β-H elimination is highly chemoselectively controlled, leading to γ-substituted allyl esters, which is contrary to the traditional
The photochemistry of ring-substituted cinnamyl acetates
Fleming,Renault,Grundy,Pincock
, p. 1146 - 1154 (2007/10/03)
The photochemistry of the (E)-cinnamyl acetates ((E)-1-aryl-3-propenyl acetates, 8a-8e) with substituents H, 4-CH3O, 3-CH3O, 4-CF3, and 3-CF3, respectively, was examined in both cyclohexane and methanol solvents. Alkene isomerization (E to Z) occurred more efficiently than other reactions and evidence is presented that this process occurs from the excited triplet state. In a slower process, 1,3-migration of the acetoxy group led to the rearranged 3-aryl-3-propenyl acetate isomers (9a-9e) as the major pathway, particularly in cylohexane. In methanol, the isomeric ethers 3-aryl-3-methoxypropene (14) and 1-aryl-3-methoxypropene (15) were formed by reaction of methanol with the photochemically generated cation. The combined yield of 14 and 15 (95% and 5%, respectively) was quantitative for the 4-methoxyphenyl compound (8b). Independent irradiations of the isomers 9a-9c demonstrated that the ethers 14 and 15 were primary photoproducts from 8 and not secondary photoproducts from 9. Fluorescence quantum yields and excited singlet state lifetimes indicated that the reactions, other than the E to Z isomerization, are from the excited singlet state.
