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Tetrahedron letters
Pergamon Press
Tetrahedron letters

Pergamon Press

0040-4039

Tetrahedron letters/Journal Tetrahedron lettersSCICCRAHCI
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    Palladium-catalyzed cross-coupling of alkylindium reagent with diaryliodonium salt

    Li, Wen-XinYang, Bo-WenNa, Jin-HeRao, Weidong...
    3页
    查看更多>>摘要:The palladium-catalyzed cross-couplings of alkylindium reagents with diaryliodonium salts proceeded efficiently in the presence of tetrakis(triphenylphosphine)palladium [Pd(PPh3)(4)], 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (SPhos), lithium tert-butoxide, and lithium chloride in DMA/THF (1:1) at 100 C, leading to the corresponding cross-coupling products in moderate to good yield with broad substrate scope and wide functional group tolerance. (C)& nbsp;2022 Elsevier Ltd. All rights reserved.

    De novo synthesis of polysubstituted 6-naphthylamines via Tf2O-mediated [4+2] annulation of amides with alkynes

    Hu, XiaoyanHao, ShuanghongWei, YanWang, Zu-Li...
    4页
    查看更多>>摘要:A conceptually new strategy has been described for the mild and environmentally friendly preparation of 6-naphthylamines via Tf2O-activated cyclization of amides with alkynes. Both terminal and internal alkynes could serve as effective nucleophiles in this transformation. This chemistry features simple reaction conditions, high chemoselectivities, wide substrate scope, and offers a practical approach to polysubstituted 6-naphthylamines.(C) 2022 Elsevier Ltd. All rights reserved.

    Metal-free synthesis of 5-trifluoromethyltetrazoles

    Lin, XiLuo, BeibeiHe, WenqinLu, Qingkai...
    4页
    查看更多>>摘要:An efficient transition-metal-free method for the synthesis of 5-trifluoromethyltetrazoles from arenediazonium tetrafluoroborates is reported, which relies on the use of trifluoroacetaldehyde N-tosylhydra-zone as a convenient 2,2,2-trifluorodiazoethane source. The reaction proceeds in good to excellent yields and shows a high functional group tolerance.CO 2022 Elsevier Ltd. All rights reserved.

    Faster and greener parallel chemical reaction work-up using 'sponge' extraction

    Li, TingtingXu, Bo
    6页
    查看更多>>摘要:We report a significantly faster and greener technique for parallel chemical reaction work-ups. Unlike conventional liquid-liquid extraction-based work-ups, we use a cylindrical-shaped polyurethane foam 'sponge' as a "foam solvent" to extract organic products from a quenched aqueous reaction mixture. The foam, loaded with organic products, serves as a convenient input for flash chromatographic separa-tions (and, therefore, we call it 'Fast2Flash'). This technique displayed a high efficiency for separating an organic phase from an aqueous phase, eliminating tedious and solvent-wasting liquid-liquid extractions and emulsion formation. Moreover, parallel and automatic operations are facilitated.(c) 2022 Published by Elsevier Ltd.

    Synthesis of 6,7-benzene-fused tropane derivatives from isoindoline-aminal hybrid compound

    Tsujihara, TetsuyaSasaki, RyotaFukkoshi, MizukiHatakeyama, Sae...
    4页
    查看更多>>摘要:Herein, the synthesis of 6,7-benzene-fused tropane derivatives from isoindoline-aminal hybrid compound has been reported. In the present synthetic study, ring-closing metathesis (RCM) was employed to construct the 6,7-benzene-fused tropene skeleton. To obtain the desired cis-1-allyl-3-stylylisoindoline precursor for the RCM reaction, the diastereoselective aza-Hosomi-Sakurai allylation and functional group transformations of isoindoline-aminal hybrid compound were performed. Using the synthesized 6,7-benzene-fused tropene derivative as a versatile precursor, synthesis of several 6,7-benzene-fused tropane derivatives was demonstrated by the transformations of the internal alkene moiety.(c) 2022 Elsevier Ltd. All rights reserved.

    Organocatalytic enantioselective electrophilic amination of benzoyl butyrolactones

    Xu, Yan-LiWang, Yu-XiaWen, Gen-FaDa, Chao-Shan...
    6页
    查看更多>>摘要:Organocatalytic electrophilic amination of benzoyl butyrolactones with azodicarboxylates was demonstrated to highly efficiently prepare quaternary carbon stereocenter-bearing alpha-amino-gamma-butyrolactones, key framework in numerous bioactive compounds. The squaramide C3 realized the highest yield (99%) and enantioselectivity (93%).(c) 2022 Elsevier Ltd. All rights reserved.

    Visible light-induced radical cascade reaction of acryloylbenzamides with N-hydroxyphthalimide esters

    Cai, XingxingLiu, YihuoDing, SiyuFu, Jiahui...
    4页
    查看更多>>摘要:An efficient and mild cascade reaction of acryloylbenzamides with N-hydroxyphthalimide (NHPI) esters is disclosed. It goes through radical addition and subsequent cyclization to give 4-alkylated isoquinolinediones in the presence of visible light and photocatalyst Ir[dF(CF3)ppy(2)](dtbbpy)PF6.(C) 2022 Elsevier Ltd. All rights reserved.

    Stereoselective synthesis of 2-deoxy-2-disubstituted ribonolactones through a TiCl4-mediated Evans-Aldol reaction

    Liu, HeYang, WenjiaoZheng, ShaojiuHe, Yang...
    6页
    查看更多>>摘要:A convenient and novel route for the stereoselective synthesis of 3,5-Di-O-benzoyl-2-deoxy-2-chloro-2-C-methyl-D-ribono-c-lactone 5a and its analogues is developed by an Evans-Aldol reaction in the presence of TiCl4. Starting from 2-chloropropionyl chloride, 5a is efficiently and regioselectively produced on a kilogram scale in an overall yield of 32% with an HPLC purity of 98% by area. In addition, this approach allowed an efficient synthesis of 3,5-Di-O-benzoyl-2-deoxy-2-fluoro-2-C-methyl-D-ribono-c- lactone 5b in a total 20% yield. (C)& nbsp;2022 Elsevier Ltd. All rights reserved.

    Functionalized styrene synthesis via palladium-catalyzed C-C cleavage of aryl ketones

    Zhang, XuWang, Zhen-YuWang, XingXu, Hui...
    4页
    查看更多>>摘要:We report herein the synthesis of functionalized styrenes via palladium-catalyzed Suzuki-Miyaura cross-coupling reaction between aryl ketone derivatives and potassium vinyltrifluoroborate. The employment of pyridine-oxazoline ligand was the key to the cleavage of unstrained C-C bond. A variety of functional groups and biologically important moleculars were well tolerated. The orthogonal Suzuki-Miyaura cou-pling demonstrated the synthetic practicability.(c) 2022 Elsevier Ltd. All rights reserved.

    Organocatalytic one-pot asymmetric synthesis of 6-trifluoromethyl-substituted 7,8-dihydrochromen-6-ol

    Nakashima, KosukeMinai, AsakoOkuaki, YuichiMatsushima, Yasuyuki...
    5页
    查看更多>>摘要:A squaramide organocatalyst efficiently promoted the asymmetric Friedel-Crafts alkylation of oc,6-unsat-urated trifluoromethyl ketones with aromatic alcohols in a one-pot procedure, affording corresponding 6trifluoromethyl-substituted 7,8-dihydrochromen-6-ol derivatives (up to 94% yield, 74% ee). (C)& nbsp;& nbsp;2022 Elsevier Ltd. All rights reserved.