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Tetrahedron letters
Pergamon Press
Tetrahedron letters

Pergamon Press

0040-4039

Tetrahedron letters/Journal Tetrahedron lettersSCICCRAHCI
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    Efficient synthesis of alpha-Nitro-beta-Dialdimine ligands via Equilibrium-Controlling approach

    Nakabayashi, MahiroNishiwaki, NagatoshiIto, AkitakaHayashi, Shotaro...
    4页
    查看更多>>摘要:Reactions of beta-formyl-beta-nitroenamine with anilines afforded N,N'-diaryl-alpha-nitro-beta-dialdimines; however, only small amounts of dialdimines were obtained when anilines possessing an electron-withdrawing group were employed. This disadvantage was overcome by adding anilinium salts to control the equilibrium, which resulted in the formation of dialdimines in considerably improved yields. This method facilitated to introduce less nucleophilic 5-bromopyrid-2-yl groups that are expected to be a precursor for various frameworks. The prepared dialdimines served as a ligand which formed the nickel(II) complex with a distorted tetrahedral structure. (C) 2022 Elsevier Ltd. All rights reserved.

    Two new dimeric benzofuran diastereomers from the roots of Eupatorium heterophyllum

    Hu, YimingSaito, YoshinoriMatsuo, YosukeGong, Xun...
    5页
    查看更多>>摘要:A pair of novel epimers of benzofuran dimers (1 and 2), together with two known compounds that were considered to be their monomeric precursor, was isolated from the methanol extract of the roots of Eupatorium heterophyllum. The structures of 1 and 2 were elucidated by 1D and 2D NMR, HRFABMS, and DFT calculations of their NMR data, including DP4+ and CP3 analysis, which assisted in determining of their relative configurations. The absolute configurations of the dimers were determined by TDDFT cal-culations of their ECD spectra. (c) 2022 Elsevier Ltd. All rights reserved.

    Ionic melting salt imidazole hydrochloride mediated the decarboxylation of (hetero)aromatic carboxylic acids

    Wang, YinXu, PingLi, YanwuWu, Yue...
    5页
    查看更多>>摘要:Imidazole hydrochloride, a hydrochloric acid carrier, was used to mediate the decarboxylation of orthopara position amino-substituted aromatic acids and nitrogen-containing heterocyclic acids, which gave excellent yields within a short time. In addition, the method can be well adapted to a gram scale, and the imidazole hydrochloride additives can be appropriately recovered for secondary utilization. (c) 2022 Elsevier Ltd. All rights reserved.

    Conformationally locked cis-1,2-diaminocyclohexane-based chiral ligands for asymmetric catalysis

    van Beek, CarimSamoshin, Vyacheslav V.
    5页
    查看更多>>摘要:An efficient synthesis for a new conformationally locked chiral cis-1,2-diaminocyclohexane scaffold has been developed. The conformational lock allows for convenient symmetrical derivatization of the amino groups through the reductive amination strategy. A series of optically pure chiral ligands based on the cis-DACH scaffold has been generated to demonstrate a proof-of-concept for these ligands as chiral catalysts in the asymmetric Henry reaction. Excellent yields with moderate enantioselectivity were demonstrated at room temperature, with an increase in enantioselectivity at lower temperatures, showing the potential of this new type of cis-DACH ligand.(c) 2022 Elsevier Ltd. All rights reserved.

    An efficient one-pot, three-component route to novel push-pull 1,3-benzodithiol-2-ylidenes via copper-catalyzed bis-C-S bond formation

    Kumar, YogendraPalluruthiyil, Mary AntonyIniyavan, PethaperumalIla, Hiriyakkanavar...
    6页
    查看更多>>摘要:An efficient one-pot, three-component synthesis of novel push-pull 1,3-benzodithiol-2-ylidenes, involv-ing reaction of active methylene compounds with CS2 in the presence of NaH as the base, followed by in situ Cu-catalyzed bis-C-S coupling of the resulting dithioate salts with 1-bromo-2-iodobenzenes has been reported. The methodology involves readily available starting materials and tolerates a broad range of functional groups. (C) 2022 Elsevier Ltd. All rights reserved.

    A turn-on fluorescent probe for palladium(II) detection with a large Stokes shift and lysosomes-targeting ability

    Wang, DonghuiHou, HaoranChen, WenlongWu, Yingnan...
    5页
    查看更多>>摘要:Although a number of palladium(II) probes have been developed, most of them have small Stokes shifts and lack good subcellular targeting ability. In this paper, a reaction-based probe (DCF-MPYM-Pd) has been designed and synthesized for palladium(II) detection. The probe was constructed by a fluorescein derivative as the fluorophore and an allyl ester group as the recognition group. The probe exhibited fast response time (5 min), high sensitivity and specificity. Importantly, it has a large Stokes shift and lysoso-mal targeting capability. In addition, it was demonstrated that the probe can be used to sense palladium (II) in living cells and can accumulate specifically in lysosomes.(c) 2022 Elsevier Ltd. All rights reserved.

    Transtion-metal-free access to 2-arylphenethylamines through aryldiazonium ion catalyzed ring-opening of aziridines with arenes

    Feng, YunqiuHuai, MenglinHuang, TianGao, Minghui...
    3页
    查看更多>>摘要:Aryldiazonium ions have been proven to catalyze effective cleavage of aziridines for the installation of varied aryl groups, providing access to a variety of 2-arylphenethylamines. This highly regioselective pro-cess, which can be performed at gram-scale, enjoys operational simplicity, as well as mild and metal-free conditions.(c) 2022 Elsevier Ltd. All rights reserved.

    Transition-Metal-Free Synthesis of Symmetrical 1,4-Diarylsubstituted 1,3-Diynes by Iodine-Mediated Decarboxylative Homocoupling of Arylpropiolic Acids

    Ghosh, SubhankarChattopadhyay, Shital Kumar
    5页
    查看更多>>摘要:An efficient metal-free method for the synthesis of symmetrical 1,3-diynes through iodine-mediated decarboxylative homocoupling of aryl propiolic acids was developed. This iodine-mediated decarboxyla-tive homocoupling reaction by Csp-Csp bond formation in DMSO underwent smoothly to afford the cor-responding 1,4-disubstituted 1,3-dialkynes in good to excellent yields. This operationally simple and environmentally benign protocol avoids the use of sophisticated ligands, additional oxidants and expen-sive transition metal/reagents.(c) 2022 Elsevier Ltd. All rights reserved.

    Acceleration effect of mild organocatalytic system 2,2'-biphenol/B(OH)(3) for 2-aza-Cope rearrangement

    Sugimoto, KenjiYoshida, RyogaMatsuya, Yuji
    4页
    查看更多>>摘要:Organocatalysis by the combination of weak acids, namely, 2,20-biphenol and B(OH)3, for 2-aza-Cope rearrangement is described. Aldehydes and 1,1-diphenyl homoallylamine were converted into the corre-sponding homoallylamines in moderate-to-high yield in the presence of 10 mol% 2,20-biphenol and 30 mol% B(OH)3. In contrast to the conventional 2-aza-Cope rearrangement catalyzed by strong activa-tors, a user-and environment-friendly organocatalytic system was established using a combination of inexpensive, easy-to-handle, non-hazardous, and bench-stable reagents.(c) 2022 Elsevier Ltd. All rights reserved.

    Amino acids in electrochemical metal-free benzylic C-H amidation

    Strekalova, SofiaKononov, AlexanderBudnikova, Yulia
    7页
    查看更多>>摘要:This report describes the mild electrochemical metal-, oxidant-, additive-free site-selective direct C-H amidation of benzyl C(sp3)-H bonds in an undivided cell using a-amino acids as a source of an amide bond moiety. Practically significant amides are obtained under electrochemical mild one-pot conditions (without strong external oxidants, at room temperature), with total yields up to 73%. This electrochem-ical approach features a functional selectivity and a broad scope of substrates with benzyl bond and dif-ferent amino acids.(c) 2022 Elsevier Ltd. All rights reserved.