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91.
Controlled dilithiation of propargyl bromide with two equivalents of n-butyllithium, in the presence of TMEDA, produces the operational equivalent of the dianion 1,3-dilithiopropyne. The latter reacts efficiently with acid chlorides to produce bishomopropargylic alcohols in a single step route and with high regioselectivity and moderate yields. 相似文献
92.
Weimin Shi Jingjie Zhang Fengqian Zhao Wei Wei Fang Liang Yin Zhang Prof. Dr. Shaolin Zhou 《Chemistry (Weinheim an der Bergstrasse, Germany)》2020,26(65):14823-14827
In this work, a mild and transition-metal-free approach for the nucleophilic aromatic substitution (SNAr) of unactivated fluoroarenes with primary aliphatic amines to form aromatic amines is reported. This reaction is facilitated by the formation of cationic fluoroarene radical intermediates in the presence of an acridinium-based organic photocatalyst under blue-light irradiation. Various electron-rich and electron-neutral fluoroarenes are competent electrophiles for this transformation. A wide range of primary aliphatic amines, including amino acid esters, dipeptides, and linear and branched amines are suitable nucleophiles. The synthetic utility of this protocol is demonstrated by the late-stage functionalization of several complex drug molecules. 相似文献
93.
Kapil Mohan Saini Rakesh K. Saunthwal Sushmita Akhilesh K. Verma 《Chemistry (Weinheim an der Bergstrasse, Germany)》2020,26(5):1017-1021
Transition-metal-free regioselective synthesis of functionalized amino-indenones by the reaction of ortho-alkynylaldehydes with a broad range of primary amines by intramolecular cyclization has been described. The designed reaction proceeds through KOH-mediated Prins-type cyclization and DMSO-promoted oxidation of the cyclopent-2-en-1-one system. The proposed mechanism and role of solvent were well supported by control experiments. For the first time, we have disclosed the reverse reactivity of (2-alkynyl)-arylaldimines in a super basic system. 相似文献
94.
The multicomponent Amine-Aldehyde-Dienophile reaction is optimized employing benzyl or 4-methoxybenzylamine. The interest of the transformation consist in the synthesis of polysubstituted cyclohex-2-enylamines. The study of the scope of this AAD process is carried out, as well as the diastereoselective version, employing commercially available chiral benzylic amines and a maleimide with the chiral information at the N-substituent. VCD spectroscopy is a very useful tool for the determination of the absolute configuration of the isolated enantiomerically enriched compounds. 相似文献
95.
Dr. Rebecca L. Greenaway Dr. Valentina Santolini Dr. Filip T. Szczypiński Dr. Michael J. Bennison Dr. Marc A. Little Andrew Marsh Dr. Kim E. Jelfs Prof. Andrew I. Cooper 《Chemistry (Weinheim an der Bergstrasse, Germany)》2020,26(17):3718-3722
Molecular dumbbells with organic cage capping units were synthesised via a multi-component imine condensation between a tri-topic amine and di- and tetra-topic aldehydes. This is an example of self-sorting, which can be rationalised by computational modelling. 相似文献
96.
Amit Vijay Sasane Dr. Antony Sekar Kulandai Raj Tzu-Hsuan Chao Dr. Mu-Jeng Chen Dr. Rai-Shung Liu 《Chemistry (Weinheim an der Bergstrasse, Germany)》2020,26(70):16932-16938
Gold-catalyzed oxidations of propargyl alcohols with nitrones by using a P(tBu)2(o-biphenyl)Au+ catalyst, afforded bicyclic annulation products from the Mannich reactions of gold enolates. The same reactions of propargyl amines with nitrones by using the same gold catalyst gave distinct oxoarylation products. Our DFT calculations indicate that oxidation of propargyl alcohols with nitrones by using electron-rich gold catalysts lead only to gold carbenes, which can generate gold enolates or oxoarylation intermediates with enolate species having a barrier smaller than that of oxoarylation species. 相似文献
97.
Wei Xu Dr. Karoly Kozma Tianxiang Sha Yi-Jen Wu Prof. May Nyman Prof. Michael M. Lerner 《Chemistry (Weinheim an der Bergstrasse, Germany)》2020,26(36):8101-8104
The alkaline earth metals (M=Mg, Ca, Sr, and Ba) exhibit a +2 oxidation state in nearly all known stable compounds, but MI dimeric complexes with M−M bonding, [M2(en)2]2+, (en=ethylenediamine) of all these metals can be stabilized within the galleries of donor-type graphite intercalation compounds (GICs). These metals can also form GICs with more conventional metal (II) ion complexes, [M(en)2]2+. Here, the facile interconversion between dimeric-MI and monomeric-MII intercalates upon the addition/removal of en are reported. Thermogravimetry, powder X-ray diffraction, and pair distribution function analysis of total scattering data support the presence of either [M2(en)2]2+ or [M(en)2]2+ guests. This phase conversion requires coupling graphene and metal redox centers, with associated reversible M−M bond formation within graphene galleries. This chemistry allows the facile isolation of unusual oxidation states, reveals M0→M2+ reaction pathways, and present new opportunities in the design of hybrid conversion/intercalation materials for applications such as charge storage. 相似文献
98.
Naghmeh Esfandiary Farzane Pazoki Athar Nakisa Kobra Azizi Iman Radfar Akbar Heydari 《应用有机金属化学》2020,34(8):e5725
A highly efficient Fe3O4@VitB1–Ag(I) magnetic catalyst has been obtained using surface modification of Fe3O4. To this end, silver chloride was immobilized on Fe3O4 nanoparticles via vitamin B1 biomolecules. The synthesized biocompatible magnetic catalyst was applied in an A3-coupling reaction in the presence of aldehyde, amine and phenyl acetylene under solvent-free conditions and afforded the desired products in excellent yields. Also, interactions between metal and ligand in the Fe3O4@VitB1–Ag(I) were studied using theoretical calculations. 相似文献
99.
Metal‐Free Reaction of ortho‐Carbonylated Alkynyl‐Substituted Arylaldehydes with Common Amines: Selective Access to Functionalized Isoindolinone and Indenamine Derivatives
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Dr. Ziping Cao Hongbo Zhu Dr. Xin Meng Jun Guan Qiang Zhang Laijin Tian Xuejun Sun Guang Chen Prof. Dr. Jinmao You 《Chemistry (Weinheim an der Bergstrasse, Germany)》2016,22(47):16979-16985
Herein we describe a reaction of ortho‐carbonylated alkynyl‐substituted arylaldehydes with common primary amines that can provide functionalized isoindolinone and 3‐hydroxylindenamine products in high yields. Depending on the substituent size of primary amines, two distinct reaction pathways were exploited selectively, that are, an initial aza‐conjugate addition followed by hydrogen transfer to access isoindolinone framework and a unique oxa‐conjugate addition followed by Petasis–Ferrier rearrangement to afford indenamine derivatives. In the presence of Et3N, the reaction property of small primary amines was changed, proceeding to afford 3‐hydroxylindenamine derivatives efficiently. These products contain interesting substructures that exist in many natural products and bioactive molecules. The reaction features contain the use of transition‐metal‐free catalysts, simple operation, broad substrate scope, and product diversity. 相似文献
100.
Franklin A. Davis Bin Yang Jianghe Deng Yongzhong Wu Yulian Zhang Ashwin Rao 《Phosphorus, sulfur, and silicon and the related elements》2013,188(5-6):1109-1117
Abstract Sulfinimine-derived polyfunctionalized chiral building blocks, often prepared in one pot, provide efficient access, with a minimum of chemical manipulation, to enantiopure, multifunctional amine derivatives including piperidines and pyrrolidines. 相似文献