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Organic & biomolecular chemistry
Royal Society of Chemistry Publications
Organic & biomolecular chemistry

Royal Society of Chemistry Publications

周刊

1477-0520

Organic & biomolecular chemistry/Journal Organic & biomolecular chemistryCCRSCI
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    Innovative green oxidation of amines to imines under atmospheric oxygen

    Yuki YamamotoShintaro KodamaAkihiro NomotoAkiya Ogawa...
    9503-9521页
    查看更多>>摘要：In recent years, the development of environmentally benign molecular construction methods has been of great importance, and especially, resource recycling, high atomic efficiency, and low environmental impact are in high demand. From this point of view, attention has also been focused on the development of one-pot synthesis of Pharmaceuticals and functional molecules. Imines are excellent synthetic intermediates of these useful molecules, and the environmentally friendly oxidative synthesis of imines from amines has been energetically developed using oxygen (or air), which is abundantly available on the Earth, as an oxidant. This review focuses on the latest innovative and green oxidation systems of amines to imines under atmospheric oxygen, and their application to one-pot/eco-friendly and sustainable synthesis of Pharmaceuticals and functional molecules. In particular, catalytic systems that activate molecular oxygen are categorized and described in detail as transition metal catalytic systems, photoirradiated catalytic systems, and organocatalytic systems.
      原文链接:
    • NETL
    • NSTL
    • Royal Soc Chemistry

    Transition metal-catalyzed double C_(vinyl)-H bond activation: synthesis of conjugated dienes

    Vipin K. MaikhuriJyotirmoy MaitySmriti SrivastavaAshok K. Prasad...
    9522-9588页
    查看更多>>摘要：Conjugated dienes have occupied a pivotal position in the field of synthetic organic chemistry and medicinal chemistry. They act as important synthons for the synthesis of various biologically important molecules and therefore, gain tremendous attention worldwide. A wide range of synthetic routes to access these versatile molecules have been developed in the past decades. Transition metal-catalyzed cross-dehydrogenative coupling (CDC) has emerged as one of the utmost front-line research areas in current synthetic organic chemistry due to its high atom economy, efficiency, and viability. In this review, an up-to-date summary including scope, limitations, mechanistic studies, stereoselectivities, and synthetic applications of transition metal-catalyzed double C_(vinyl)-H bond activation for the synthesis of conjugated dienes has been reported since 2013. The literature reports mentioned in this review have been classified into three different categories, i.e. (a) C_(vinyl)-Cinyi bond formation via oxidative homo-coupling of terminal alkenes; (b) C_(vinyl)-C_(Vinyl) bond formation via non-directed oxidative cross-coupling of linear/cyclic alkenes and terminal/internal alkenes, and (c) C_(vinyl)-C_(vinyl) bond formation via oxidative cross-coupling of directing group bearing alkenes and terminal/internal alkenes. Overall, this review aims to provide a concise overview of the current status of the considerable development in this field and is expected to stimulate further innovation and research in the future.
      原文链接:
    • NETL
    • NSTL
    • Royal Soc Chemistry

    Lawesson's reagent promoted deoxygenation of azlactones for the syntheses of 2,4-disubstituted thiazoles

    Gaofeng YinXiaodong WangYuqing WangTao Shi...
    9589-9592页
    查看更多>>摘要：Azlactones and thiazoles are common structural motifs and possess diverse applications. A new method for the efficient and straightforward syntheses of 2,4-disubstituted thiazoles from azlactones has been developed. The reaction proceeded via deoxygenation of azlactones by Lawesson's reagent without metal or external additives. A variety of 2,4-disubstituted thiazoles were synthesized with up to 92% yield. Furthermore, the importance of this methodology was also justified by a gram-scale synthesis.
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    • NETL
    • NSTL
    • Royal Soc Chemistry

    Divergent cyclodimerizations of styrylnaphthols under aerobic visible-light irradiation and Bronsted acid catalysis

    Jiyuan LyuAurelie ClarazPascal RetailleauGeraldine Masson...
    9593-9599页
    查看更多>>摘要：Dimeric cyclization reactions show great potential to rapidly form highly substituted complex cyclic molecules from simple starting materials. However, such an appealing process is often hampered by the lack of selectivity. Herein we report two divergent cyclodimerization reactions of l-styrylnaphthalen-2-ol derivatives under simple and very mild reaction conditions. A stereoselective visible light-induced oxidative (1 + 1 + 4 + 4) homodimerization gave rise to highly substituted 1,5-dioxocanes in moderate yields. This transformation harnessed singlet oxygen as a safe and mild oxidant under photocatalyst-free reaction conditions. Additionally, we demonstrated that the same substrates undergo a (4 + 2) heterodimerization under Bronsted-acid catalysis to produce chromane derivatives featuring 3 contiguous tertiary stereocenters in good to high yields with excellent diastereoselectivities.
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    • NETL
    • NSTL
    • Royal Soc Chemistry

    Trifluoromethylated thermally activated delayed fluorescence molecule as a versatile photocatalyst for electron-transfer- and energy-transfer-driven reactions

    Tatsuya MorofujiTakuma KurokawaYouhei ChitoseChihaya Adachi...
    9600-9603页
    查看更多>>摘要：In this study, we propose that the trifluoromethylated thermally activated delayed fluorescent molecule 4[Cz(CF_3)_2]IPN is a versatile organic photocatalyst that can be used for electron-transfer-driven reactions requiring a photocatalyst with high oxidizing power and energy-transfer-driven reactions that require an Ir photocatalyst. 4[Cz(CF_3)_2]IPN was used in radical reactions via electron transfer and dearomative cycloaddition reactions via energy transfer.
      原文链接:
    • NETL
    • NSTL
    • Royal Soc Chemistry

    Transition metal-free annulative vinylene transfer via the 1,3-dipolar reaction of N-ylides: access to benzo-fused indolizines

    Limin ZhaoWen LiJiali LiuLinying Ni...
    9604-9608页
    查看更多>>摘要：An efficient metal-free annulative vinylene transfer protocol for the synthesis of benzo-fused indolizines via 1,3-dipolar cycloaddi-tions of N-ylides with vinylene carbonate has been developed. Vinylene carbonate serves as an acetylene surrogate without any external oxidant involved. This transformation leads to the direct construction of versatile benzo-fused indolizine derivatives in moderate to good yields.
      原文链接:
    • NETL
    • NSTL
    • Royal Soc Chemistry

    Total synthesis of Myxoprincomide, a secondary metabolite from Myxococcus xanthus

    Michael KohrChristine WaltJan DastbazRolf Mueller...
    9609-9612页
    查看更多>>摘要：Myxoprincomide, a secondary metabolite of the myxobacterium Myxococcus xanthus DK 1622, is synthesised for the first time. The central, unusual a-ketoamide is generated at the end of the synthesis to avoid side reactions during the synthesis of this rather reactive subunit. Nevertheless, the synthetic natural product is obtained as an isomeric mixture. Detailed analytical investigations show that the identical isomeric mixture is found in the isolated natural product.
      原文链接:
    • NETL
    • NSTL
    • Royal Soc Chemistry

    Tandem reduction and trifluoroethylation of quinolines and quinoxalines with trifluoroacetic acid and trimethylamine borane

    Yi-Na LiMing-Xi ZhouJin-Bo WuZhen Wang...
    9613-9617页
    查看更多>>摘要：A metal-free tandem reduction and N-trifluoroethylation of quinolines and quinoxalines has been developed. It provided a convenient route to access trifluoroethylated tetrahydroquinolines and tetrahydroquinoxalines. This one-pot method avoids the purification process of the intermediate. Mechanistically, the in situ-generated boryl acetal species reacted with tetrahydroquinolines to generate iminiums followed by reduction to give the target compounds.
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    • NETL
    • NSTL
    • Royal Soc Chemistry

    Direct synthesis of tetrahydropyran-4-ones via O_3ReOH-catalyzed Prins cyclization of 3-chloro-homoallylic alcohols

    Kwanruthai TadpetchPongsit VijitphanSasiwan KaewsenAticha Thiraporn...
    9618-9624页
    查看更多>>摘要：A new variation of Prins cyclization to directly and stereoselectively synthesize c/s-2,6-disubstituted tetrahydropyran-4-ones from 3-chlorohomoallylic alcohols and aldehydes catalyzed by perrhe-nic acid is reported. The reaction is generally compatible with a range of aliphatic and aromatic aldehydes and 24 examples of tet-rahydropyran-4-one products have been prepared in moderate to good yields. This methodology highlights the use of simple starting materials and commercially available aqueous perrhenic acid as a catalyst for Prins cyclization reactions to directly synthesize 2,6-di-substituted tetrahydropyran-4-ones.
      原文链接:
    • NETL
    • NSTL
    • Royal Soc Chemistry

    Host-guest synergistic enhancement of antibacterial effect by a supra molecular strategy

    Mengke MaJunyi ChenYahan ZhangXinbei Du...
    9625-9628页
    查看更多>>摘要：A supramolecular synergistic antibacterial strategy involving direct complexation of a commercial antibacterial agent, azelaic acid (AzA) by a cationic pillar[5]arene (WP5A) is described. The formation of AzA/WP5A complex could exert synergistic antibacterial effect, leading to promote wound healing efficacy and reduce bacterial burden on 5. aureus-infected mice models.
      原文链接:
    • NETL
    • NSTL
    • Royal Soc Chemistry