19819-94-4Relevant articles and documents
Photo-Ni-Dual-Catalytic C(sp2)-C(sp3) Cross-Coupling Reactions with Mesoporous Graphitic Carbon Nitride as a Heterogeneous Organic Semiconductor Photocatalyst
Antonietti, Markus,Ghosh, Indrajit,K?nig, Burkhard,Khamrai, Jagadish,Savateev, Aleksandr
, p. 3526 - 3532 (2020/04/09)
The synergistic combination of a heterogeneous organic semiconductor mesoporous graphitic carbon nitride (mpg-CN) and a homogeneous nickel catalyst with visible-light irradiation at room temperature affords the C(sp2)-C(sp3) cross-co
Development of highly electron-deficient and less sterically-hindered phosphine ligands possessing 1,3,5-triazinyl groups
Abe, Kazumi,Kitamura, Masanori,Fujita, Hikaru,Kunishima, Munetaka
, p. 87 - 93 (2018/01/05)
Highly electron-deficient and less sterically-hindered phosphine ligands with two or three 1,3,5-triazinyl groups on the phosphorus atoms have been synthesized and examined in transition metal-catalyzed reactions for the first time. Due to the lack of any hydrogens or substituents at ortho-positions of the 1,3,5-triazine towards the phosphorous atom, it is considered that the steric hindrance of the tris(triazinyl)phosphine ligand to a metal center is least among triarylphosphine ligands. In the Stille coupling of aryl iodides, these electron-poor phosphine ligands provided good product yields compared to hitherto well-known phosphine ligands.
The transition-metal-catalyst-free oxidative homocoupling of organomanganese reagents prepared by the insertion of magnesium into organic halides in the presence of MnCl2·2LiCl
Peng, Zhihua,Li, Na,Sun, Xinyang,Wang, Fang,Xu, Lanjian,Jiang, Cuiyu,Song, Linhua,Yan, Zi-Feng
, p. 7800 - 7809 (2014/12/10)
Organomanganese reagents were prepared by the insertion of magnesium into aryl halides in the presence of MnCl2·2LiCl. These organomanganese reagents smoothly undergo 1,2-addition, acylation, and Pd-catalyzed cross-coupling with various electrophiles. Especially, the oxidative homocoupling of organomanganese reagents was completed in one pot without an additional transition-metal catalyst.
Palladium-catalyzed allyl cross-coupling reactions with in situ generated organoindium reagents
Lee, Kooyeon,Kim, Hyunseok,Mo, Juntae,Lee, Phil Ho
scheme or table, p. 2147 - 2157 (2011/10/31)
Inter- and intramolecular palladium-catalyzed allyl cross-coupling reactions, using allylindium generated in situ from allyl halides and indium, is demonstrated. Allylindium compounds may be effective nucleophilic coupling partners in palladium-catalyzed cross-coupling reactions. A variety of allyl halides, such as allyl iodide, allyl bromide, crotyl bromide, prenyl bromide, geranyl bromide, and 3-bromocyclohexene afforded the allylic cross-coupling products in good to excellent yields. Stereochemistry of the double bond is retained in the allylic cross-coupling reactions. Electrophilic cross-coupling partners, such as aryl and vinyl halides, dibromoolefin, alkynyl iodide, and aryl and vinyl triflates participate in these reactions. The presence of various substituents, such as n-butyl, ketal, acetyl, ethoxycarbonyl, nitrile, N-phenylamido, nitro, and chloride groups on the aromatic ring of electrophilic coupling partners showed little effect on the efficiency of the reactions. The present conditions work equally well for not only intermolecular but also intramolecular palladium-catalyzed cross-coupling reactions. These methods provide an efficient synthetic method for the introduction of an allyl group, which can be easily further functionalized to afford an sp2- and sp-hybridized carbon. The present method complements existing synthetic methods as a result of advantageous features such as easy preparation and handling, thermal stability, high reactivity and selectivity, operational simplicity, and low toxicity of allylindium reagents.
Carboxylation of alkylboranes by N-heterocyclic carbene copper catalysts: Synthesis of carboxylic acids from terminal alkenes and carbon dioxide
Ohishi, Takeshi,Zhang, Liang,Nishiura, Masayoshi,Hou, Zhaomin
supporting information; experimental part, p. 8114 - 8117 (2011/10/18)
Caught in the act: N-Heterocyclic carbene copper(I) complexes (1; IPr=1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene) serve as an excellent catalyst for the carboxylation of alkylboranes (2; R=alkyl) with CO2 to afford a variety of functionalized carboxylic acids (3) in high yields. A novel copper methoxide/alkylborane adduct (A) and its subsequent CO2 insertion product (B) have been isolated and shown to be true active catalyst species.
Ionic liquid supported organotin reagents: Green tools for stille cross-coupling reactions with brominated substrates
Louaisil, Nicolas,Pham, Phuoc Dien,Boeda, Fabien,Faye, Djibril,Castanet, Anne-Sophie,Legoupy, Stephanie
supporting information; experimental part, p. 143 - 149 (2011/03/18)
Efficiency of ionic liquid supported organotin reagents in Stille cross-coupling reactions involving aryl bromides has been investigated. In a general manner, products were isolated with good yields by using a very simple catalytic system without the need of solvent, ligand, or additives. The organotin compounds were recycled without loss of activity and the contamination by tin was limited and controlled ([Sn] 3 ppm). Clean tin's good! Efficiency of ionic liquid supported organotin reagents in Stille cross-coupling reactions involving aryl bromides has been investigated. Products were isolated with good yields by using a verysimple catalytic system. Organotin compounds were recycled without loss of activity and the contamination by tin was limited ([Sn] 3 ppm).
A general and efficient suzuki-miyaura cross-coupling protocol using weak base and no water: The essential mole of acetate
Wang, Bing,Sun, Hui-Xia,Sun, Zhi-Hua
experimental part, p. 3688 - 3692 (2009/12/03)
A weak base, CsOAc, promotes Suzuki-Miyaura cross-coupling and related Pd-catalyzed reactions under anhydrous conditions as effectively as stronger bases. Aryl triflates exhibit unusual reaction rates, which are comparable to that: of bromoarenes. A negle
Xantphos as an efficient ligand for palladium-catalyzed cross-coupling reactions of aryl bromides and triflates with allyl acetates and indium
Seomoon, Dong,Phil, Ho Lee
, p. 1165 - 1168 (2008/09/18)
(Chemical Equation Presented) Xantphos was found to be an efficient ligand for palladium-catalyzed allyl cross-coupling reactions of aryl bromides and triflates with allylindium reagents generated in situ from allyl acetates and indium. These reactions occur in high yield with good functional group tolerance.
Inter- and intramolecular palladium-catalyzed allyl cross-coupling reactions using allylindium generated in situ from allyl acetates, indium, and indium trichloride
Seomoon, Dong,Lee, Kooyeon,Kim, Hyunseok,Lee, Phil Ho
, p. 5197 - 5206 (2008/02/10)
Inter- and intramolecular palladium-catalyzed ally! cross-coupling reactions using allylindium generated in situ by treatment of allyl acetates with indium and indium trichloride in the presence of Pd0 catalyst and nBuNMe2 in DMF were successfully demonstrated. Allylindium species generated in situ by reductive transmetalation of π- allylpalladium(II) complexes, obtained from a variety of allyl acetales in the presence of Pd0 catalyst together with indium and indium trichloride, were found to be capable of acting as effective nucleophilic coupling partners in Pd-catalyzed cross-coupling reactions. A variety of allyl acetates such as but-l-en-3-yl acetate, crotyl acetate, and 2-methylallyl acetate afforded the corresponding allylic compounds in good yields in cross-coupling reactions. Various electrophilic cross-coupling partners such as aryl iodides and vinyl bromides and triflates participate in these reactions. Not only intermolecular but also intramolecular Pd-catalyzed cross-coupling reactions work equally well to produce the desired allylic coupling products in good yields.
Phosphazene base-promoted halogen-zinc exchange reaction of aryl iodides using diethylzinc
Ueno, Masahiro,Wheatley, Andrew E. H.,Kondo, Yoshinori
, p. 3549 - 3550 (2008/09/19)
The use of catalytic t-Bu-P4 base dramatically improved the performance of halogen-zinc exchange of aryl iodides, and the arylzinc derivatives were functionalized under copper-free reaction conditions. The Royal Society of Chemistry 2006.
