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  • 1.
    Jiang, Tuo
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Quan, Xu
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Zhu, Can
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Andersson, Pher G.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-E.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Palladium-Catalyzed Oxidative Synthesis of a-Acetoxylated Enones from Alkynes2016In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 55, no 19, p. 5824-5828Article in journal (Refereed)
    Abstract [en]

    We report a palladium-catalyzed oxidative functionalization of alkynes to generate -acetoxylated enones in one step. A range of functional groups are well-tolerated in this reaction. Mechanistic studies, including the use of O-18-labeled DMSO, revealed that the ketone oxygen atom in the product originates from DMSO.

  • 2.
    Li, Man-Bo
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry. Anhui University, P. R. China.
    Posevins, Daniels
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Geoffroy, Antoine
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Zhu, Can
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-E.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Efficient Heterogeneous Palladium-Catalyzed Oxidative Cascade Reactions of Enallenols to Furan and Oxaborole Derivatives2020In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 59, no 5, p. 1992-1996Article in journal (Refereed)
    Abstract [en]

    A heterogeneous palladium-catalyzed oxidative cyclization of enallenols has been developed for the construction of highly substituted furan and oxaborole derivatives. The heterogeneous catalyst (Pd-AmP-MCF) exhibits high activity, high site- and stereoselectivity, and efficient palladium recyclability in the transformations.

  • 3.
    Qiu, Youai
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Yang, Bin
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Jiang, Tuo
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Zhu, Can
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-E.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Palladium-Catalyzed Oxidative Cascade Carbonylative Spirolactonization of Enallenols2017In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 56, no 12, p. 3221-3225Article in journal (Refereed)
    Abstract [en]

    A highly selective palladium-catalyzed oxidative carbonylation/carbocyclization/alkoxycarbonylation of enallenols to afford spirolactones bearing an all-carbon quaternary center was developed. This transformation involves the overall formation of three C-C bonds and one C-O bond through a cascade insertion of carbon monoxide (CO), an olefin, and CO. Preliminary experiments on chiral anion-induced enantioselective carbonylation/carbocyclization of enallenols afforded spirolactones with moderate enantioselectivity.

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  • 4.
    Qiu, Youai
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Yang, Bin
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Zhu, Can
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-E.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Highly Efficient Cascade Reaction for Selective Formation of Spirocyclobutenes from Dienallenes via Palladium-Catalyzed Oxidative Double Carbocyclization-Carbonylation-Alkynylation2016In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 138, no 42, p. 13846-13849Article in journal (Refereed)
    Abstract [en]

    A highly selective cascade reaction that allows the direct transformation of dienallenes to spirocyclobutenes (spiro[3.4]octenes) as single diastereoisomers has been developed. The reaction involves formation of overall four C-C bonds and proceeds-via a palladium-catalyzed oxidative transformation with insertion of olefin, olefin, and carbon monoxide. Under slightly different reaction conditions, an additional CO insertion takes place to give spiro[4.4]nonenes with formation of overall five C-C bonds.

  • 5.
    Qiu, Youai
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Yang, Bin
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Zhu, Can
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-E.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Highly selective olefin-assisted palladium-catalyzed oxidative carbocyclization via remote olefin insertion2017In: Chemical Science, ISSN 2041-6520, E-ISSN 2041-6539, Vol. 8, no 1, p. 616-620Article in journal (Refereed)
    Abstract [en]

    A highly selective olefin-assisted palladium-catalyzed oxidative carbocyclization via remote olefin insertion to afford cyclohexenes has been developed. It was shown that the assisting olefin moiety was indispensable for the formation of the cyclohexene product. Furthermore, preliminary studies on chiral anion-induced asymmetrical carbocyclization-borylation of enallenes have been carried out.

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  • 6.
    Qiu, Youai
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Yang, Bin
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Zhu, Can
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-E.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Palladium-Catalyzed Oxidative Carbocyclization–Borylation of Enallenes to Cyclobutenes2016In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 55, no 22, p. 6520-6524Article in journal (Refereed)
    Abstract [en]

    A highly efficient palladium-catalyzed oxidative borylation of enallenes was developed for the selective formation of cyclobutene derivatives and fully-substituted alkenylboron compounds. Cyclobutenes are formed as the exclusive products in MeOH in the presence of H2O and Et3N, whereas the use of AcOH leads to alkenylboron compounds. Both reactions showed a broad substrate scope and good tolerance for various functional groups, including carboxylic acid ester, free hydroxy, imide, and alkyl groups. Furthermore, transformations of the borylated products were conducted to show their potential applications.

  • 7.
    Yang, Bin
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Qiu, Youai
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Jiang, Tuo
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Wulff, William D.
    Yin, Xiaopeng
    Zhu, Can
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-E.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Enantioselective Palladium-Catalyzed Carbonylative Carbocyclization of Enallenes via Cross-Dehydrogenative Coupling with Terminal Alkyne: Efficient Construction of a-Chirality of Ketones2017In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 56, no 16, p. 4535-4539Article in journal (Refereed)
    Abstract [en]

    An enantioselective PdII/Brønsted acid-catalyzed carbonylative carbocyclization of enallenes ending with a cross-dehydrogenative coupling (CDC) with a terminal alkyne was developed. VAPOL phosphoric acid was found as the best co-catalyst among the examined 28 chiral acids, for inducing the enantioselectivity of α-chiral ketones. As a result, a number of chiral cyclopentenones were easily synthesized in good to excellent enantiomeric ratio with good yields.

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  • 8.
    Yang, Bin
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Zhu, Can
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Qiu, Youai
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-E.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Enzyme- and Ruthenium-Catalyzed Enantioselective Transformation of alpha-Allenic Alcohols into 2,3-Dihydrofurans2016In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 55, no 18, p. 5568-5572Article in journal (Refereed)
    Abstract [en]

    An efficient one-pot method for the enzyme- and ruthenium-catalyzed enantioselective transformation of alpha-allenic alcohols into 2,3-dihydrofurans has been developed. The method involves an enzymatic kinetic resolution and a subsequent ruthenium-catalyzed cycloisomerization, which provides 2,3-dihydrofurans with excellent enantioselectivity (up to >99%ee). A ruthenium carbene species was proposed as a key intermediate in the cycloisomerization.

  • 9.
    Zhu, Can
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-E.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    An Efficient Approach to Regio- and Stereodefined Fully-Substituted Alkenylsilanes by Pd-Catalyzed Allenic C(sp(3))-H Oxidation2019In: Chemistry: A European Journal, ISSN 0947-6539, Vol. 25, no 49, p. 11566-11573Article in journal (Refereed)
    Abstract [en]

    A highly efficient palladium-catalyzed functionalization of allenylsilanes to give regio- and stereodefined fully-substituted alkenylsilanes has been developed. This oxidative coupling reaction showed good functional group compatibility with exclusive regio- and stereoselectivity. The pending olefin on the silyl group was shown to be an indispensable element for the initial allenic C(sp(3))-H bond cleavage, and performs as the directing group to control the overall selectivity. The addition of substoichiometric amounts of Et3N was found to increase the reaction rate leading to a higher reaction yield. The reaction can be easily scaled up and applied for the late-stage functionalization of natural products and pharmaceutical compounds, including amino acids and steroid derivatives. The newly introduced functional groups include aryl, alkynyl, and boryl groups. The highly strained four-membered ring, silacyclobutene was obtained when B(2)pin(2) was employed as the coupling partner. Mechanistic studies, including kinetic isotope effects, showed that the allenic C(sp(3))-H bond cleavage is the rate-limiting step.

  • 10.
    Zhu, Can
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Liu, Jie
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Khanh Mai, Binh
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Himo, Fahmi
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-E
    Stockholm University, Faculty of Science, Department of Organic Chemistry. Mid Sweden University, Sweden.
    Efficient Stereoselective Carbocyclization to cis-1,4-Disubstituted Heterocycles Enabled by Dual Pd/Electron Transfer Mediator (ETM) Catalysis2020In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 142, no 12, p. 5751-5759Article in journal (Refereed)
    Abstract [en]

    An efficient Pd/ETM (ETM = electron transfer mediator)-cocatalyzed stereoselective oxidative carbocyclization of dienallenes under aerobic oxidation conditions has been developed to afford six-membered heterocycles. The use of a bifunctional cobalt complex [Co(salophen)-HQ] as hybrid ETM gave a faster aerobic oxidation than the use of separated ETMs, indicating that intramolecular electron transfer between the hydroquinone unit and the oxidized metal macrocycle occurs. In this way, a class of important cis-1,4-disubstituted six-membered heterocycles, including dihydropyran and tetrahydropyridine derivatives were obtained in high diastereoselectivity with good functional group compatibility. The experimental and computational (DFT) studies reveal that the pendent olefin does not only act as an indispensable element for the initial allene attack involving allenic C(sp(3))-H bond cleavage, but it also induces a face-selective reaction of the olefin of the allylic group, leading to a highly diastereoselective formation of the product. Finally, the deuterium kinetic isotope effects measured suggest that the initial allenic C(sp(3))-H bond cleavage is the rate-limiting step, which was supported by DFT calculations.

  • 11.
    Zhu, Can
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Liu, Jie
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Li, Man-Bo
    Stockholm University, Faculty of Science, Department of Organic Chemistry. Anhui University, China.
    Bäckvall, Jan-E.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Palladium-catalyzed oxidative dehydrogenative carbonylation reactions using carbon monoxide and mechanistic overviews2020In: Chemical Society Reviews, ISSN 0306-0012, E-ISSN 1460-4744, Vol. 49, no 2, p. 341-353Article, review/survey (Refereed)
    Abstract [en]

    Carbon monoxide, which is an abundant and inexpensive carbonyl source, has been widely applied to synthesize carbonyl-containing compounds, for example ketones, esters, and amides. These types of compounds are ubiquitous in natural products, pharmaceuticals, as well as in functional materials. This review focuses on the palladium-catalyzed dehydrogenative C-H/X-H (X = C, N, O) carbonylation transformations under oxidative conditions. The related C-H bonds here include C(sp)-H, C(sp(2))-H, and C(sp(3))-H bonds. From a step- and atom-economy perspective, transition metal-catalyzed oxidative dehydrogenative C-H/X-H carbonylation reactions with CO constitute one of the most efficient strategies for the construction of versatile carbonyl groups, without the requirement of pre-functionalized substrates.

  • 12.
    Zhu, Can
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Yang, Bin
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-E.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Highly Selective Cascade C-C Bond Formation via Palladium-Catalyzed Oxidative Carbonylation-Carbocyclization-Carbonylation-Alkynylation of Enallenes2015In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 137, no 37, p. 11868-11871Article in journal (Refereed)
    Abstract [en]

    A highly efficient palladium-catalyzed oxidative cascade reaction of enallenes undergoing overall four C-C bond formations has been developed. The insertion cascade proceeds via carbonylation carbocyclization carbonylation alkynylation involving sequential insertion of carbon monoxide, olefin, and carbon monoxide. Furthermore, different types of terminal alkynes and functionalized enallenes have been investigated and found to undergo the cascade reaction under mild reaction conditions.

  • 13.
    Zhu, Can
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Yang, Bin
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Jiang, Tuo
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-E.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Olefin-Directed Palladium-Catalyzed Regio- and Stereoselective Oxidative Arylation of Allenes2015In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 54, no 31, p. 9066-9069Article in journal (Refereed)
    Abstract [en]

    An olefin-directed palladium-catalyzed oxidative regio- and stereoselective arylation of allenes to afford 1,3,6-trienes has been established. A number of functionalized allenes, including 2,3- and 3,4-dienoates and 3,4-dienol derivatives, have been investigated and found to undergo the olefin-directed allene arylation. The olefin moiety has been proven to be a crucial element for the arylating transformation.

  • 14.
    Zhu, Can
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Yang, Bin
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Khanh Mai, Binh
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Palazzotto, Sara
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Qiu, Youai
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Gudmundsson, Arnar
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Ricke, Alexander
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Himo, Fahmi
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-E
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Highly Selective Palladium-Catalyzed Hydroborylative Carbocyclization of Bisallenes to Seven-Membered Rings2018In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 140, no 43, p. 14324-14333Article in journal (Refereed)
    Abstract [en]

    A highly selective palladium-catalyzed hydroborylative carbocyclization of bisallenes to afford seven-membered rings has been established. This ring-closing coupling reaction showed good functional group compatibility with high chemo- and regioselectivity, as seven-membered ring 3 was the only product obtained. The extensive use of different linkers, including nitrogen, oxygen, malononitrile, and malonate, showed a broad substrate scope for this approach. A one-pot cascade reaction was realized by trapping the primary allylboron compound with an aldehyde, affording a diastereomerically pure alcohol and a quaternary carbon center by formation of a new C-C bond. A comprehensive mechanistic DFT investigation is also presented. The calculations suggest that the reaction proceeds via a concerted hydropalladation pathway from a Pd(0)-olefin complex rather than via a pathway involving a defined palladium hydride species. The reaction was significantly accelerated by the coordination of the pendant olefin, as well as the introduction of suitable substituents in the bridge, due to the Thorpe-Ingold effect.

  • 15.
    Zhu, Can
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Yang, Bin
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Qiu, Youai
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-E.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Highly Selective Construction of Seven-Membered Carbocycles by Olefin-Assisted Palladium-Catalyzed Oxidative Carbocyclization-Alkoxycarbonylation of Bisallenes2016In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 55, no 46, p. 14405-14408Article in journal (Refereed)
    Abstract [en]

    An olefin-assisted palladium-catalyzed oxidative carbocyclization-alkoxycarbonylation of bisallenes to afford seven-membered carbocycles has been established. This dehydrogenative coupling reaction showed excellent substrate scope and functional group compatibility. The reaction exhibited high chemo-and regioselectivity, and ester 3 was the only product obtained. The olefin unit has been proven to be indispensable during the reaction. Moreover, intramolecular oxidative coupling suggests that the reaction proceeds via a (pallyl)palladium intermediate.

  • 16.
    Zhu, Can
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Yang, Bin
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Qiu, Youai
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-E.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Olefin-Directed Palladium-Catalyzed Regio- and Stereoselective Hydroboration of Allenes2016In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 22, no 9, p. 2939-2943Article in journal (Refereed)
    Abstract [en]

    An olefin-directed palladium-catalyzed regio- and stereoselective hydroboration of allenes has been developed to afford fully substituted alkenylboron compounds. The reaction showed a broad substrate scope: a number of functionalized allenes, including 2,3-dienoate, 3,4-dienoate, 3,4-dienol, 1,2-allenylphosphonate, and alkyl-substituted allenes, could be used in this olefin-directed allene hydroboration. The olefin unit was proven to be an indispensable element for this transformation.

1 - 16 of 16
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