36707-32-1Relevant academic research and scientific papers
"bulky-Yet-Flexible" α-Diimine Palladium-Catalyzed Reductive Heck Cross-Coupling: Highly Anti-Markovnikov-Selective Hydroarylation of Alkene in Air
Yang, Xu-Wen,Li, Dong-Hui,Song, A-Xiang,Liu, Feng-Shou
, p. 11750 - 11765 (2020/10/23)
To pursue a highly regioselective and efficient reductive Heck reaction, a series of moisture-and air-stable α-diimine palladium precatalysts were rationally designed, readily synthesized, and fully characterized. The relationship between the structures of the palladium complexes and the catalytic properties was investigated. It was revealed that the"bulky-yet-flexible"palladium complexes allowed highly anti-Markovnikov-selective hydroarylation of alkenes with (hetero)aryl bromides under aerobic conditions. Further synthetic application of the present protocol could provide rapid and straightforward access to functional and biologically active molecules.
Chemoselective Hydrogenation of Alkynes to (Z) -Alkenes Using an Air-Stable Base Metal Catalyst
Zubar, Viktoriia,Sklyaruk, Jan,Brzozowska, Aleksandra,Rueping, Magnus
supporting information, p. 5423 - 5428 (2020/07/24)
A highly selective hydrogenation of alkynes using an air-stable and readily available manganese catalyst has been achieved. The reaction proceeds under mild reaction conditions and tolerates various functional groups, resulting in (Z)-alkenes and allylic alcohols in high yields. Mechanistic experiments suggest that the reaction proceeds via a bifunctional activation involving metal-ligand cooperativity.
Application of novel coupling reaction to preparing carbon-carbon bond structured compounds
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Paragraph 0074-0078, (2019/06/30)
The invention relates to application of a novel coupling reaction to preparing carbon-carbon bond structured compounds and mainly provides a reaction between alkyl indium compounds and halides. The reaction between the alkyl indium compounds and the halides can produce corresponding carbon-carbon structured products. The novel coupling reaction is high in process yield, broad in functional group tolerance and good in compatibility.
Sterically hindered N-heterocyclic carbene/palladium(ii) catalyzed Suzuki-Miyaura coupling of nitrobenzenes
Chen, Kai,Chen, Wei,Yi, Xiaofei,Chen, Wanzhi,Liu, Miaochang,Wu, Huayue
supporting information, p. 9287 - 9290 (2019/08/08)
Palladium-catalyzed denitrative Suzuki coupling of nitroarenes using 2-aryl-5-(2,4,6-triisopropylphenyl)-2,3-imidazolylidene[1,5-a]pyridines as the ligands is described. The key to success is the use of the NHC ligands which show strong donating ability and suitable steric hindrance allowing the successful oxidative addition of Ar-NO2 bonds. Both aromatic and aliphatic boronic acids are tolerated, and a variety of biphenyls and alkylarenes were obtained in good to excellent yields.
Cesium carbonate-catalyzed indium insertion into alkyl iodides and their synthetic utilities in cross-coupling reactions
Feng, Xue-Xin,Wu, Zhen,Wang, Qing-Dong,Chen, Bing-Zhi,Rao, Weidong,Yang, Jin-Ming,Shen, Zhi-Liang
, (2019/07/31)
A catalytic amount of cesium carbonate (10?mol%) was found to be capable of effectively catalyzing the insertion of indium powder into alkyl iodides. The thus-generated alkyl indium reagents could readily undergo palladium-catalyzed cross-coupling reactions with a wide variety of aryl halides, showing compatibility to a range of important functional groups.
Preparation of Alkyl Indium Reagents by Iodine-Catalyzed Direct Indium Insertion and Their Applications in Cross-Coupling Reactions
Zhi, Man-Ling,Chen, Bing-Zhi,Deng, Wei,Chu, Xue-Qiang,Loh, Teck-Peng,Shen, Zhi-Liang
, p. 3017 - 3023 (2019/02/26)
An efficient method for the synthesis of alkyl indium reagent by means of an iodine-catalyzed direct indium insertion into alkyl iodide in THF is reported. The thus-generated alkyl indium reagents effectively underwent Pd-catalyzed cross-coupling reactions with various aryl halides, exhibiting good compatibility to a variety of sensitive functional groups. By replacing THF with DMA and using 0.75 equiv of iodine, less reactive alkyl bromide could be used as substrate for indium insertion with equal ease.
Copper(II)-catalyzed preparation of alkylindium compounds and applications in cross-coupling reactions both in aqueous media
Wang, Peng,Chen, Bing-Zhi,Guo, Yi-Cong,Rao, Weidong,Shen, Zhi-Liang
supporting information, (2019/11/11)
An efficient water-based method for the synthesis of alkylindium compound in the presence of a catalytic amount of cheap and readily available CuSO4·5H2O (10 mol%) was developed. The thus-generated alkylindium compounds effectively underwent palladium-catalyzed cross-coupling reactions with a myriad of aryl halides in aqueous media, leading to the cross-coupled products in modest to high yields. The mildness of the formed alkyl organometallics allowed the tolerance to various important functional groups incorporated in both substrates of alkyl iodides and aryl halides.
Cobalt(II)-catalyzed preparation of alkylindium reagents and applications in cross-coupling with aryl halides
Wang, Peng,Song, Xuan-Di,Chen, Bing-Zhi,Rao, Weidong,Shen, Zhi-Liang
, (2019/10/16)
The direct insertion of indium powder into alkyl iodides was found to be efficiently catalyzed by a catalytic amount of cobalt(II) bromide (10 mol%). Upon subjection of the thus-formed alkylindium compounds to palladium-catalyzed cross-coupling reactions with a wide range of aryl halides, a series of cross-coupled products could be obtained in moderate to good yields with the tolerance to many important functional groups.
Nickel-Catalyzed C(sp2)?C(sp3) Kumada Cross-Coupling of Aryl Tosylates with Alkyl Grignard Reagents
Piontek, Aleksandra,Och?dzan-Siod?ak, Wioletta,Bisz, Elwira,Szostak, Michal
supporting information, p. 2329 - 2336 (2019/04/13)
Aryl tosylates are an attractive class of electrophiles for cross-coupling reactions due to ease of synthesis, low price, and the employment of C?O electrophiles, however, the reactivity of aryl tosylates is low. Herein, we report the Ni-catalyzed C(sp2)?C(sp3) Kumada cross-coupling of aryl tosylates with primary and secondary alkyl Grignard reagents. The method delivers valuable alkyl arenes by cross-coupling with challenging alkyl organometallics possessing β-hydrogens that are prone to β-hydride elimination and homo-coupling. The reaction is catalyzed by an air- and moisture stable-Ni(II) precatalyst. A broad range of electronically-varied aryl tosylates, including bis-tosylates, underwent this transformation, and many examples are suitable at mild room temperature conditions. The combination of Ar?X cross-coupling with the facile Ar?OH activation/cross-coupling strategy permits for orthogonal cross-coupling with challenging alkyl organometallics. Furthermore, we demonstrate that the method operates with TON reaching 2000, which is one of the highest turnovers observed to date in Ni-catalyzed cross-couplings. (Figure presented.).
Nickel-Catalyzed Csp2-Csp3 Bond Formation via C-F Bond Activation
Ho, Yee Ann,Leiendecker, Matthias,Liu, Xiangqian,Wang, Chengming,Alandini, Nurtalya,Rueping, Magnus
supporting information, p. 5644 - 5647 (2018/09/12)
A nickel-catalyzed cross coupling of aryl fluorides via C-F bond activation has been developed. The alkylation method allows selective replacement of aryl fluorides by alkyl groups and enables the synthesis of diverse and otherwise difficult to access scaffolds in good yields.
