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1.
Tristan Delcaillau Prof. Dr. Bill Morandi 《Chemistry (Weinheim an der Bergstrasse, Germany)》2021,27(46):11823-11826
A nickel-catalyzed thiolation of aryl nitriles has been developed to access functionalized aryl thioethers. The ligand dcype (1,2-bis(dicyclohexylphosphino)ethane) as well as the base KOtBu (potassium tert-butoxide) are essential to achieve this transformation. This scalable and practical process involves both a C−C bond activation and a C−S bond formation. Furthermore, this reaction shows a high functional-group tolerance and enables the late-stage functionalization of important molecules. 相似文献
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Nurtalya Alandini Luca Buzzetti Gianfranco Favi Tim Schulte Lisa Candish Karl D. Collins Paolo Melchiorre 《Angewandte Chemie (International ed. in English)》2020,59(13):5248-5253
Herein, we report a one‐electron strategy for catalytic amide synthesis that enables the direct carbamoylation of (hetero)aryl bromides. This radical cross‐coupling approach, which is based on the combination of nickel and photoredox catalysis, proceeds at ambient temperature and uses readily available dihydropyridines as precursors of carbamoyl radicals. The method's mild reaction conditions make it tolerant of sensitive‐functional‐group‐containing substrates and allow the installation of an amide scaffold within biologically relevant heterocycles. In addition, we installed amide functionalities bearing electron‐poor and sterically hindered amine moieties, which would be difficult to prepare with classical dehydrative condensation methods. 相似文献
3.
Dongyang Han Sasa Li Siqi Xia Mincong Su Prof. Dr. Jian Jin 《Chemistry (Weinheim an der Bergstrasse, Germany)》2020,26(54):12349-12354
An efficient and operationally simple Ni-catalyzed amination protocol has been developed. This methodology features a simple NiII salt, an organic base and catalytic amounts of both a pyridinium additive and Zn metal. A diverse number of (hetero)aryl halides were coupled successfully with primary and secondary alkyl amines, and anilines in good to excellent yields. Similarly, benzophenone imine gave the corresponding N-arylation product in an excellent yield. 相似文献
4.
Ryan T. McGuire Connor M. Simon Dr. Arun A. Yadav Dr. Michael J. Ferguson Prof. Dr. Mark Stradiotto 《Angewandte Chemie (Weinheim an der Bergstrasse, Germany)》2020,132(23):9037-9041
The development of Ni-catalyzed C−N cross-couplings of sulfonamides with (hetero)aryl chlorides is reported. These transformations, which were previously achievable only with Pd catalysis, are enabled by use of air-stable ( L )NiCl(o-tol) pre-catalysts (L= PhPAd-DalPhos and PAd2-DalPhos ), without photocatalysis. The collective scope of (pseudo)halide electrophiles (X=Cl, Br, I, OTs, and OC(O)NEt2) demonstrated herein is unprecedented for any reported catalyst system for sulfonamide C−N cross-coupling (Pd, Cu, Ni, or other). Preliminary competition experiments and relevant coordination chemistry studies are also presented. 相似文献
5.
Justin S. Marcum Tiffany R. Taylor Prof. Simon J. Meek 《Angewandte Chemie (Weinheim an der Bergstrasse, Germany)》2020,132(33):14174-14179
A catalytic method for the site-selective and enantioselective synthesis of functionalized arenes by the intermolecular hydroarylation of terminal and internal 1,3-dienes with aryl pinacolato boronates is reported. The reactions are promoted by 5.0 mol % of a readily available monodentate phosphoramidite-Ni complex in ethanol, affording a variety of enantioenriched products in up to 96 % yield and 99:1 er. Mechanistic studies indicate that Ni–allyl formation is irreversible and related to the nature of the arylboronate. 相似文献
6.
Ming-Yu Chen Sylvain Charvet Dr. Pierre-Adrien Payard Dr. Marie-Eve L. Perrin Dr. Julien C. Vantourout 《Angewandte Chemie (Weinheim an der Bergstrasse, Germany)》2024,136(2):e202311165
A robust electrochemically driven nickel-catalyzed halogen exchange of unsaturated halides and triflates (Br to Cl, I to Cl, I to Br, and OTf to Cl) is reported. A combination of NiCl2 ⋅ glyme as the precatalyst, 2,2′-bipyridine as a ligand, NMP as the solvent, and electrochemistry allowed the generation of a nickel species that promotes reductive elimination of the desired product. This paired electrochemical halogenation is compatible with a range of unsaturated halides and triflates, including heterocycles, dihaloarenes, and alkenes with good functional-group tolerance. Joint experimental and theoretical mechanistic investigations highlighted three catalytic events: i) oxidative addition of the aryl halide to a Ni(0) species to deliver a Ni(II) intermediate; ii) halide metathesis at Ni(II); iii) electrochemical oxidation of Ni(II) to Ni(III) to enable the formation of the desired aryl halide upon reductive elimination. This methodology allows the replacement of heavy halogens (I or Br) or polar atoms (O) with the corresponding lighter and more lipophilic Cl group to block undesired reactivity or modify the properties of drug and agrochemical candidates. 相似文献
7.
Palladium‐Catalyzed Synthesis of (Hetero)Aryl Alkyl Sulfones from (Hetero)Aryl Boronic Acids,Unactivated Alkyl Halides,and Potassium Metabisulfite 下载免费PDF全文
Andre Shavnya Dr. Kevin D. Hesp Dr. Vincent Mascitti Dr. Aaron C. Smith 《Angewandte Chemie (International ed. in English)》2015,54(46):13571-13575
A palladium‐catalyzed one‐step synthesis of (hetero)aryl alkyl sulfones from (hetero)arylboronic acids, potassium metabisulfite, and unactivated or activated alkylhalides is described. This transformation is of broad scope, occurs under mild conditions, and employs readily available reactants. A stoichiometric experiment has led to the isolation of a catalytically active dimeric palladium sulfinate complex, which was characterized by X‐ray diffraction analysis. 相似文献
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Dorus Heijnen Dr. Jean‐Baptiste Gualtierotti Dr. Valentín Hornillos Prof. Dr. Ben L. Feringa 《Chemistry (Weinheim an der Bergstrasse, Germany)》2016,22(12):3991-3995
Nickel‐catalyzed selective cross‐coupling of aromatic electrophiles (bromides, chlorides, fluorides and methyl ethers) with organolithium reagents is presented. The use of a commercially available nickel N‐heterocyclic carbene (NHC) complex allows the reaction with a variety of (hetero)aryllithium compounds, including those prepared via metal‐halogen exchange or direct metallation, whereas a commercially available electron‐rich nickel‐bisphosphine complex smoothly converts alkyllithium species into the corresponding coupled product. These reactions proceed rapidly (1 h) under mild conditions (room temperature) while avoiding the undesired formation of reduced or homocoupled products. 相似文献
10.
过渡金属催化的偶联反应是构筑C-C键的高效方法,在有机合成中得到了广泛的应用.然而,相对于Heck反应、Negishi偶联与Suzuki偶联等构筑C(sp2)-C(sp2)键的反应,过渡金属催化的构筑C(sp3)-C(sp3)键的偶联反应较难进行,发展较晚.近年来,烷基-烷基C-C键偶联反应受到广泛的重视,一些高效催化剂被开发出来,其中镍催化剂展示出独特的催化活性和选择性.本文将综述镍催化烷基-烷基C-C键偶联反应最新研究进展,主要包括烷基亲电试剂与金属有机试剂交叉偶联反应、导向基参与的C(sp3)-H键活化的偶联反应、镍-光反应催化剂协同催化偶联反应、烷基亲电试剂与亲电试剂的还原偶联反应和镍催化烯烃加成反应等. 相似文献
11.
The Sonogashira coupling of terminal acetylenes with aryl iodides, catalyzed by Ni-Cu, in the presence of sodium lauryl sulfate as the surfactant and cesium carbonate as the base, in water, leads to the formation of aryl alkyne products. 相似文献
12.
A combinatorial nickel-catalyzed monofluoroalkylation of aryl bromides with the industrial raw regent ethyl chlorofluoroacetate has been developed. The two key factors to successful conversion are the combination of nickel with readily available nitrogen and phosphine ligands and the using of a mixture of different solvents. Mechanistic investigations indicated a new zinc regent might generated in situ and be involved in the reaction process. 相似文献
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Ferdinand H. Lutter Lucie Grokenberger Philipp Spieß Jeffrey M. Hammann Konstantin Karaghiosoff Paul Knochel 《Angewandte Chemie (International ed. in English)》2020,59(14):5546-5550
A combination of 10 % CoCl2 and 20 % 2,2′‐bipyridine ligands enables cross‐coupling of functionalized primary and secondary alkylzinc reagents with various (hetero)aryl halides. Couplings with 1,3‐ and 1,4‐substituted cycloalkylzinc reagents proceeded diastereoselectively leading to functionalized heterocycles with high diastereoselectivities of up to 98:2. Furthermore, alkynyl bromides react with primary and secondary alkylzinc reagents providing the alkylated alkynes. 相似文献
15.
We report a new method for a tandem Pd-catalyzed intramolecular addition of active methylene compounds to internal alkynes followed by coupling with aryl and heteroaryl bromides. Highly substituted vinylidenecyclopentanes were obtained with good yields, complete selectivity, and excellent functional group tolerance. A plausible mechanism, supported by DFT calculations, involves the oxidative addition of bromoarene to Pd(0), followed by cyclization and reductive elimination. The excellent regio- and stereoselectivity arises from the 5-exo-dig intramolecular addition of the enol form of the substrate to alkyne activated by the π-acidic Pd(II) center, postulated as the rate-determining step. 相似文献
16.
Andre Shavnya Kevin D. Hesp Vincent Mascitti Aaron C. Smith 《Angewandte Chemie (Weinheim an der Bergstrasse, Germany)》2015,127(46):13775-13779
A palladium‐catalyzed one‐step synthesis of (hetero)aryl alkyl sulfones from (hetero)arylboronic acids, potassium metabisulfite, and unactivated or activated alkylhalides is described. This transformation is of broad scope, occurs under mild conditions, and employs readily available reactants. A stoichiometric experiment has led to the isolation of a catalytically active dimeric palladium sulfinate complex, which was characterized by X‐ray diffraction analysis. 相似文献
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Ke-Jin Jiao Dong Liu Dr. Hong-Xing Ma Hui Qiu Ping Fang Prof. Dr. Tian-Sheng Mei 《Angewandte Chemie (Weinheim an der Bergstrasse, Germany)》2020,132(16):6582-6586
A highly regioselective Ni-catalyzed electrochemical reductive relay cross-coupling between an aryl halide and an alkyl halide has been developed in an undivided cell. Various functional groups are tolerated under these mild reaction conditions, which provides an alternative approach for the synthesis of 1,1-diarylalkanes. 相似文献
19.
Kirsten A. Hewitt Claire A. Herbert Alissa C. Matus Elizabeth R. Jarvo 《Molecules (Basel, Switzerland)》2021,26(19)
Herein, we report a Kumada cross-coupling reaction of benzylic sulfonamides. The scope of the transformation includes acyclic and cyclic sulfonamide precursors that cleanly produce highly substituted acyclic fragments. Preliminary data are consistent with a stereospecific mechanism that allows for a diastereoselective reaction. 相似文献