82598-07-0Relevant academic research and scientific papers
Copper-free palladium-catalysed desulfinative homocoupling of sodium arylsulfinates under mild and aerobic conditions
Zhang, Wei
, p. 1 - 3 (2017)
A Pd(II)-catalysed homocoupling of sodium arylsulfinates has been successfully achieved under mild conditions. This transformation is a new method for the homocoupling reaction of sodium arylsulfinates, thus providing an alternative synthesis of symmetric biaryls. The reported homocoupling reaction is tolerant to many common functional groups, such as ester, halo, cyano and nitro and works well in the presence of electron-donating and electron-withdrawing substituents. Notably, the reported desulfinative homocoupling does not require Cu salts, ligands and bases, making this newly developed transformation attractive.
Regioselectivity of the Chan–Lam coupling of ambident nitropyrazoles with trans-styrylboronic acid
Davydov, Dmitry V.,Oprunenko, Yurii F.,Sazonov, Petr K.
, p. 185 - 187 (2020)
Regioselectivity of the Chan–Lam coupling of ambident nitropyrazoles with trans-styrylboronic acid depends on the base and catalyst nature and can vary the N(1)/N(2)-isomer ratio from ～2: 1 to ～1: 2. 2-Methyl-4-nitro- and 2,4-dinitroimidazoles are unreact
Nickel-catalyzed N-vinylation of heteroaromatic amines via C-H bond activation
Landge, Vinod G.,Rana, Jagannath,Subaramanian, Murugan,Balaraman, Ekambaram
, p. 6896 - 6900 (2017)
Here, we report a ligand- and reductant-free nickel-catalyzed N-vinylation of heteroaromatic amines using biorenewable p-cymene as a solvent. This unprecedented cross-coupling strategy has high functional group tolerance (halides, alkoxy, cyano, chiral motif, etc.) and proceeded via C-H bond activation.
Synthesis of the 1,2-seco fusicoccane diterpene skeleton by Stille coupling reaction between the highly functionalized A and C ring segments of cotylenin A
Kuwata, Kazuaki,Hanaya, Kengo,Higashibayashi, Shuhei,Sugai, Takeshi,Shoji, Mitsuru
, p. 6039 - 6045 (2017)
1-Hydroxy-14-isopropyl-3β-methoxymethyl-7β,11β-dimethyl-3α-[((2-trimethylsilyl)ethoxy)methoxy]-1,2-secofusicocca-8,10(14)-dien-2-one, a highly functionalized 1,2-seco fusicoccane diterpene skeleton related to cotylenin A was synthesized in a convergent manner. The A ring segment, i. e., (1′R,2S, 2′E,5S)-2-methoxymethyl-5-[1′-methyl-3’-(trimethylstannyl)prop-2-enyl]-2-[((2″-trimethylsilyl)ethoxy)methoxy]cyclopentanone, was synthesized in 20.1% yield over 18 steps from known (S)-5-isopropenyl-2-methylcyclopent-1-enecarbaldehyde. This was coupled with the C ring segment, i. e., (R)-5-hydroxymethyl-2-isopropyl-5-methylcyclopent-1-en-1-yl trifluoromethylsulfonate, which was prepared according to our previous report. The Stille coupling reaction between alkenylstannane and sterically hindered triflate proceeded successfully in the presence of PEPPSI-SIPr (85%), and the total yield of the target molecule was 17.1% over the longest linear sequences (19 steps) from (S)-5-isopropenyl-2-methylcyclopent-1-enecarbaldehyde.
Enantioselective Rhodium-Catalyzed Alkenylation of Aliphatic Imines
Qian, Xue-Wei,Xue, Ze-Jian,Zhao, Qian,Cui, Zhe,Chen, Ya-Jing,Feng, Chen-Guo,Lin, Guo-Qiang
, p. 5601 - 5604 (2017)
An efficient, enantioselective rhodium-catalyzed addition of potassium alkenyltrifluoroborates to N-nosyl aliphatic imines has been realized. Good reaction yields and excellent enantioselectivities (94-99% ee) were obtained for a variety of aliphatic imines and nucleophilic alkenyltrifluoroborates. An active rhodium-diene catalyst and the precise reaction condition control proved to be pivotal for success.
Pd-Catalyzed Cross-Coupling of Organostibines with Styrenes to Give Unsymmetric (E)-Stilbenes and (1 E,3 E)-1,4-Diarylbuta-1,3-dienes and Fluorescence Properties of the Products
Zhang, Zhao,Zhang, Dejiang,Zhu, Longzhi,Zeng, Dishu,Kambe, Nobuaki,Qiu, Renhua
supporting information, p. 5317 - 5322 (2021/06/28)
A general and effective palladium-catalyzed cross-coupling of organostibines with styrenes to give (E)-olefins was disclosed. By the use of an organostibine reagent, this method can produce unsymmetric (E)-1,2-diarylethylenes and (1E,3E)-1,4-diarylbuta-1,3-dienes in good yields with high E/Z selectivity and good functional group tolerance. Resveratrol and DMU-212 were synthesized in high yield. The protocol can be extended to the synthesis of (1E,3E,5E)-1,6-diphenylhexa-1,3,5-triene in 40% yield. Products 5e, 5f, and 7a showed good photoluminescence quantum yields ranging from 72 to 99%.
Asymmetric Aminomethylative Etherification of Conjugated Dienes with Aliphatic Alcohols Facilitated by Hydrogen Bonding
Chang, Rui,Cai, Shoule,Yang, Guoqing,Yan, Xuyang,Huang, Hanmin
supporting information, p. 12467 - 12472 (2021/08/30)
The asymmetric construction of allylic C-O bonds with primary or secondary aliphatic alcohols remains a substantial challenge in Pd-catalyzed allylation chemistry. Here, we report the development of an additive-free, palladium-catalyzed asymmetric aminomethylative etherification of conjugated dienes that enables the efficient, asymmetric O-allylation of primary and secondary aliphatic alcohols as well as water. Mechanism studies revealed that the hydrogen-bonding interaction between the alcohol and the in situ introduced aminomethyl moiety is critical to facilitate the nucleophilic addition of the alcohol to the π-allylpalladium species, which opened up the possibility of using aliphatic alcohols and water as nucleophilic substrates. This reaction tolerates a broad range of functional groups and shows remarkable regioselectivities and uniformly high enantioselectivities, which provides a direct and rapid approach to optically pure allylic 1,3-amino ethers and 1,3-amino alcohols from simple starting materials.
Stereospecific Iron-Catalyzed Carbon (sp2)-Carbon (sp2) Cross-Coupling of Aryllithium with Vinyl Halides
Chen, Peng,Peng, Xiao-Shui,Wang, Zhi-Yong,Wong, Henry N. C.
supporting information, p. 4385 - 4390 (2021/06/27)
We present herein an efficient synthetic protocol involving iron-catalyzed cross-coupling of organolithium compounds with vinyl halides as key coupling partners. More than 30 examples were obtained with moderate to good yields and high stereoselectivities. The practicality of this method is evidenced by a gram-scale synthesis. In addition, a preliminary mechanistic investigation was also performed.
Nickel- and Palladium-Catalyzed Cross-Coupling Reactions of Organostibines with Organoboronic Acids
Zhang, Dejiang,Le, Liyuan,Qiu, Renhua,Wong, Wai-Yeung,Kambe, Nobuaki
supporting information, p. 3104 - 3114 (2020/12/11)
A strategy for the formation of antimony-carbon bond was developed by nickel-catalyzed cross-coupling of halostibines. This method has been applied to the synthesis of various triaryl- and diarylalkylstibines from the corresponding cyclic and acyclic halostibines. This protocol showed a wide substrate scope (72 examples) and was compatible to a wide range of functional groups such as aldehyde, ketone, alkene, alkyne, haloarenes (F, Cl, Br, I), and heteroarenes. A successful synthesis of arylated stibine 3 a in a scale of 34.77 g demonstrates high synthetic potential of this transformation. The formed stibines (R3Sb) were then used for the palladium-catalyzed carbon–carbon bond forming reaction with aryl boronic acids [R?B(OH)2], giving biaryls with high selectivity, even the structures of two organomoieties (R and R′) are very similar. Plausible catalytic pathways were proposed based on control experiments.
Copper quinolate: A simple and efficient catalytic complex for coupling reactions
Wu, Fengtian,Li, Huiqin,Xie, Jianwei
, (2019/11/22)
We describe an effective and novel method to prepare N-aryl imidazoles via the copper quinolate-catalyzed N-arylation of aryl halides and imidazoles. A wide range of products were obtained in moderate to excellent yields under the optimal reaction conditions. Applying standard conditions, the model reaction could be performed on a gram scale. This method also presents a new avenue to the “click” reaction of terminal alkynes, benzyl bromide, and sodium azide and to the construction of C–C bonds by homocoupling of phenylboronic acid or phenylacetylene derivatives with the aid of copper quinolate.
