107203-08-7Relevant academic research and scientific papers
Platinum-catalyzed 1,4-addition of arylboronic acids to β-substituted α,β-unsaturated ketones
Hayashi, Tamio,Sasaki, Keigo
, p. 842 - 843 (2008)
Platinum salts represented by K2PtCl4 were found to catalyze the 1,4-addition of arylboronic acids to β-substituted α,β-unsaturated ketones to give high yields of β-arylated ketones. The reaction is completed in 1h in the presence of 1 mol % of the catalyst in dioxane/H2O at 70 °C. Copyright
Electrochemical Radical Selenylation/1,2-Carbon Migration and Dowd-Beckwith-Type Ring-Expansion Sequences of Alkenylcyclobutanols
Kim, Yeon Joo,Kim, Dae Young
, p. 1021 - 1025 (2019)
Electrochemical oxidative radical selenylation/1,2-carbon migration and Dowd-Beckwith-type ring-expansion sequences of alkenylcyclobutanols were developed in this study. This approach is environmentally benign and uses shelf-stable diselenides as selenium
Chiral bis-phosphoramidites based on linked-BINOL for rhodium-catalyzed 1,4-addition of arylboronic acids to α,β-unsaturated carbonyl compounds
Yamamoto, Yasunori,Kurihara, Kazunori,Sugishita, Noriyuki,Oshita, Kengo,Piao, Dongguo,Miyaura, Norio
, p. 1224 - 1225 (2005)
Cationic rhodium(I) complex prepared from Shibasaki's linked-BINOL and [Rh(nbd)2]BF4 catalyzed asymmetric 1,4-addition of arylboronic acids to enones at room temperature with high enantioselectivities up to 99.8%ee. Copyright
N-heterocyclic carbene-rhodium(I) complexes derived from proline for the 1,4-conjugate addition of arylboronic acids to enones in neat water
Tang, Yi-Qiang,Lv, Huan,He, Xiao-Na,Lu, Jian-Mei,Shao, Li-Xiong
, p. 705 - 708 (2011)
N-Heterocyclic carbene-rhodium(I) complexes derived from N-benzyl substituted proline have been successfully synthesized and were found to be efficient catalysts for the 1,4-conjugate addition of arylboronic acids to enones in neat water at 40 °C. Under the optimal reaction conditions, all reactions gave the addition products in good to high yields.
Potassium organotrifluoroborates in rhodium-catalyzed asymmetric 1,4-additions to enones
Pucheault, Mathieu,Darses, Sylvain,Genet, Jean-Pierre
, p. 3552 - 3557 (2002)
Potassium organotrifluoroborates, highly stable organoboron derivatives, participate in asymmetric 1,4-additions to enones. This reaction, catalyzed by cationic rhodium(I) complexes chelated with binap, MeO-biphep or josiphos ligand, affords 1,4-adducts w
Palladium-Catalyzed Intermolecular Arylation of Functionally-Substituted Cycloalkenes by Aryl Iodides
Larock, Richard C.,Yum, Eul K.,Yang, Hoseok
, p. 305 - 322 (1994)
The palladium-catalyzed, intermolecular arylation of functionally-substituted cycloalkenes by aryl iodides affords a new synthetic route to a variety of arylated cyclic derivatives.The arylation of 2-cyclopenten-1-ol and 2-cyclo-hexen-1-ol provides modest yields of the corresponding 3-arylcycloalkanones, while 2-methyl-2-cyclopenten-1-ol affords a mixture of singly and doubly arylated cyclopentanone produts. 1-Acetoxycyclopentene undergoes arylation to produce the corresponding allylic aryl substitution product opening up a new route for the α-arylation of cycloalkanones.Cyclic allylic ethers undergo arylation at both ends of the C-C double bond to generate mixtures of singly arylated vinylic ethers. 1-Cyanocylopentene reacts with aryl iodides under palladium catalysis to produce 1-cyano-5-arylcyclopentenes in high yield. 2-Methyl-2-cycloalken-1-ones afford modest yields of doubly arylated 2-cycloalken-1-ones in a single step.
Pd-Catalyzed Regio- and Stereoselective sp3 C?H Arylation of Primary Aliphatic Amines: Mechanistic Studies and Synthetic Applications
Ha, Hyeonbin,Choi, Ho Jeong,Park, Hahyoun,Gwon, Yunyeong,Lee, Jiin,Kwak, Jaesung,Kim, Min,Jung, Byunghyuck
, p. 1136 - 1145 (2021)
The Pd-catalyzed γ-position sp3?C?H arylation of primary amines bearing an aliphatic chain or cycloalkyl substituent and related mechanistic studies are disclosed. 3-Bromo-2-hydroxybenzaldehyde plays a key role in γ-position sp3?C?H arylation as a transient directing group (TDG) to assist the regio- and stereoselective C?H activation of a Pd catalyst, and the development of a tandem reaction to transform 1°-amines into γ-aryl-substituted ketones demonstrates synthetic utility. Density functional theory (DFT)-based calculations revealed the detailed reaction mechanism and the origins of the high selectivity (γ-position and cis-only). The X-ray crystal structure of the isolated endo-palladacycle intermediate supported the DFT results, and a kinetic isotope experiment confirmed the results of DFT calculations indicating that the C?H activation step via simultaneous palladation and deprotonation is rate-determining.
Catalytic direct β-arylation of simple ketones with aryl iodides
Huang, Zhongxing,Dong, Guangbin
, p. 17747 - 17750 (2013)
Herein we report a direct β-arylation of simple ketones with widely available aryl iodides, combining palladium-catalyzed ketone oxidation, aryl-halide activation, and conjugate addition through a single catalytic cycle. Simple cyclic ketones with different ring-sizes, as well as acyclic ketones, can be directly arylated at the β-position with complete site-selectivity and excellent functional group tolerance.
Electrochemical Conversion of Functionalised Aryl Chlorides and Bromides to Arylzinc Species
Sibille, Soline,Ratovelomanana, Victorin,Perichon, Jacques
, p. 283 - 284 (1992)
Electroreduction of aromatic chlorides or bromides in a cell fitted with a sacrificial zinc anode, in the presence of a nickel 2,2'-bipyridine complex affords the corresponding organozinc species in good yield.
Rh-catalyzed 1,4-addition of triallyl(aryl)silanes to α,β-unsaturated carbonyl compounds
Kamei, Toshiyuki,Uryu, Mizuho,Shimada, Toyoshi
, p. 1622 - 1624 (2016)
Rh-catalyzed 1,4-addition of triallyl(aryl)silane to α,β-unsaturated carbonyl compounds was developed. Triallyl(aryl)silanes were used as air- and moisture-stable silicon nucleophiles. Allylsilanes were converted to silanols in situ and underwent transmetalation. This method can accept a wide range of functionalized triallyl(aryl)silane and α,β-unsaturated carbonyl compounds.
