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31.
Ju‐You Lu Hong Wan Jianwei Zhang Zhixuan Wang Yang Li Yongmei Du Chunying Li Prof. Zhao‐Tie Liu Prof. Zhong‐Wen Liu Prof. Jian Lu 《Chemistry (Weinheim an der Bergstrasse, Germany)》2016,22(49):17542-17546
A palladium‐catalyzed direct C‐arylation reaction of readily available cage carboranyllithium reagents with aryl halides has been developed for the first time. This method is applicable to a wide range of aryl halide substrates including aryl iodides, aryl bromides, and heteroaromatic halides. 相似文献
32.
Pd nanoparticles have been successfully supported on nanoscale metal-organic frameworks (NMOFs) by using a simple and effective microwave-assisted impregnation process. The resulting composite, representing as a highly active NMOFs supported metal nanoparticles catalyst for the Suzuki cross-coupling reaction between aryl/heteroaryl halides and arylboronic acids, is well characterized, and its high activity and good recyclability are discussed in details. It reveals that, compared to the corresponding bulk MOFs and conventional active carbon materials, nanoscale MOFs as novel support materials for heterogeneous catalysts can exhibit superior performance in the catalytic reactions. 相似文献
33.
Pd-catalyzed cross-coupling reactions of various arenediazonium salts with ArSi(OR)3 and KArBF3 have been achieved in good to excellent yields under simple aerobic conditions in water at room temperature. The functional group tolerance makes these transformations as attractive alternatives to the traditional cross-coupling approaches. Furthermore, the sequence can also be performed in a one-pot domino process, omitting the isolation of the intermediate arenediazonium salt. 相似文献
34.
Pd‐PEPPSI‐IHeptCl: A General‐Purpose,Highly Reactive Catalyst for the Selective Coupling of Secondary Alkyl Organozincs
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Dr. Bruce Atwater Dr. Nalin Chandrasoma Dr. David Mitchell Dr. Michael J. Rodriguez Prof. Michael G. Organ 《Chemistry (Weinheim an der Bergstrasse, Germany)》2016,22(41):14531-14534
Dichloro[1,3‐bis(2,6‐di‐4‐heptylphenyl)imidazol‐2‐ylidene](3‐chloropyridyl)palladium(II) (Pd‐PEPPSI‐IHeptCl), a new, very bulky yet flexible Pd–N‐heterocyclic carbene (NHC) complex has been evaluated in the cross‐coupling of secondary alkylzinc reactants with a wide variety of oxidative addition partners in high yields and excellent selectivity. The desired, direct reductive elimination branched products were obtained with no sign of migratory insertion across electron‐rich and electron‐poor aromatics and all forms of heteroaromatics (five and six membered). Impressively, there is no impact of substituents at the site of reductive elimination (i.e., ortho or even di‐ortho), which has not yet been demonstrated by another catalyst system to date. 相似文献
35.
Exploring Regioselective Bond Cleavage and Cross‐Coupling Reactions using a Low‐Valent Nickel Complex
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Addison N. Desnoyer Florian W. Friese Weiling Chiu Marcus W. Drover Dr. Brian O. Patrick Prof. Dr. Jennifer A. Love 《Chemistry (Weinheim an der Bergstrasse, Germany)》2016,22(12):4070-4077
Recently, esters have received much attention as transmetalation partners for cross‐coupling reactions. Herein, we report a systematic study of the reactivity of a series of esters and thioesters with [{(dtbpe)Ni}2(μ‐η2:η2‐C6H6)] (dtbpe=1,2‐bis(di‐tert‐butyl)phosphinoethane), which is a source of (dtbpe)nickel(0). Trifluoromethylthioesters were found to form η2‐carbonyl complexes. In contrast, acetylthioesters underwent rapid Cacyl?S bond cleavage followed by decarbonylation to generate methylnickel complexes. This decarbonylation could be pushed backwards by the addition of CO, allowing for regeneration of the thioester. Most of the thioester complexes were found to undergo stoichiometric cross‐coupling with phenylboronic acid to yield sulfides. While ethyl trifluoroacetate was also found to form an η2‐carbonyl complex, phenyl esters were found to predominantly undergo Caryl?O bond cleavage to yield arylnickel complexes. These could also undergo transmetalation to yield biaryls. Attempts to render the reactions catalytic were hindered by ligand scrambling to yield nickel bis(acetate) complexes, the formation of which was supported by independent syntheses. Finally, 2‐naphthyl acetate was also found to undergo clean Caryl?O bond cleavage, and although stoichiometric cross‐coupling with phenylboronic acid proceeded with good yield, catalytic turnover has so far proven elusive. 相似文献
36.
Svatava Voltrova 《合成通讯》2013,43(21):2473-2477
A flow preparation of chromous chloride has been introduced as a viable alternative to the batch protocol. Activity of the prepared reagent has been demonstrated in the traditional Nozaki–Hiyama–Kishi reaction. 相似文献
37.
Cross‐Coupling of Organolithium with Ethers or Aryl Ammonium Salts by C−O or C−N Bond Cleavage
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Ze‐Kun Yang Dong‐Yu Wang Hiroki Minami Hiroyuki Ogawa Takashi Ozaki Dr. Tatsuo Saito Dr. Kazunori Miyamoto Dr. Chao Wang Prof. Dr. Masanobu Uchiyama 《Chemistry (Weinheim an der Bergstrasse, Germany)》2016,22(44):15693-15699
Various aryl‐, alkenyl‐, and/or alkyllithium species reacted smoothly with aryl and/or benzyl ethers with cleavage of the inert C?O bond to afford cross‐coupled products, catalyzed by commercially available [Ni(cod)2] (cod=1,5‐cyclooctadiene) catalysts with N‐heterocyclic carbene (NHC) ligands. Furthermore, the coupling reaction between the aryllithium compounds and aryl ammonium salts proceeded under mild conditions with C?N bond cleavage in the presence of a [Pd(PPh3)2Cl2] catalyst. These methods enable selective sequential functionalizations of arenes having both C?N and C?O bonds in one pot. 相似文献
38.
Wai Chung Fu Zheng Wang Dr. Wesley Ting Kwok Chan Prof. Dr. Zhenyang Lin Prof. Dr. Fuk Yee Kwong 《Angewandte Chemie (International ed. in English)》2017,56(25):7166-7170
A versatile π-extension reaction was developed based on the three-component cross-coupling of aryl halides, 2-haloarylcarboxylic acids, and norbornadiene. The transformation is driven by the direction and subsequent decarboxylation of the carboxyl group, while norbornadiene serves as an ortho-C−H activator and ethylene synthon via a retro-Diels–Alder reaction. Comprehensive DFT calculations were performed to account for the catalytic intermediates. 相似文献
39.
Dr. He Zhao Xiu Li Rongqing Guan Prof. Huanfeng Jiang Prof. Min Zhang 《Chemistry (Weinheim an der Bergstrasse, Germany)》2019,25(69):15858-15862
The tandem dual C−H amination of tetrahydroquinoxalines with free amines under aerobic copper catalysis conditions has been demonstrated. The synthetic protocol proceeds with good substrate and functional group compatibility, mild reaction conditions, short reaction time, the use of the naturally abundant [Cu]/O2 catalyst system, excellent chemoselectivity and synthetic efficiency, and with no need for the pre-installation of specific aminating agents, which offers a practical platform for the rapid and diverse synthesis of diaminoquinoxalines. Moreover, this work has shown the potential of single-electron-oxidation-induced C−H functionalization of N-heterocycles, and its application in the development of optoelectronic materials. 相似文献
40.
Friedrich Kreyenschmidt Selim E. Meurer Prof. Dr. Konrad Koszinowski 《Chemistry (Weinheim an der Bergstrasse, Germany)》2019,25(23):5912-5921
>The combination of CoCl2 with bidentate phosphines is known to catalyze challenging cross-coupling and Heck-type reactions, but the mechanisms of these valuable transformations have not been established. Here, we use electrospray-ionization mass spectrometry to intercept the species formed in these reactions. Our results indicate that a sequence of transmetalation, reductive elimination, and redox disproportionation convert the cobalt(II) precatalyst into low-valent cobalt complexes. These species readily transfer single electrons to alkyl bromides, which thereupon dissociate into alkyl radicals and Br−. In cross-coupling reactions, the alkyl radicals add to the cobalt catalyst to form observable heteroleptic complexes, which release the coupling products through reductive eliminations. In the Heck-type reactions, the low abundance of newly formed ionic species renders the analysis more difficult. Nonetheless, our results also point to the occurrence of single-electron transfer processes and the involvement of radicals in these transformations. 相似文献