Change search
Link to record
Permanent link

Direct link
Jiang, Tuo
Publications (10 of 12) Show all publications
Yang, B., Qiu, Y., Jiang, T., Wulff, W. D., Yin, X., Zhu, C. & Bäckvall, J.-E. (2017). Enantioselective Palladium-Catalyzed Carbonylative Carbocyclization of Enallenes via Cross-Dehydrogenative Coupling with Terminal Alkyne: Efficient Construction of a-Chirality of Ketones. Angewandte Chemie International Edition, 56(16), 4535-4539
Open this publication in new window or tab >>Enantioselective Palladium-Catalyzed Carbonylative Carbocyclization of Enallenes via Cross-Dehydrogenative Coupling with Terminal Alkyne: Efficient Construction of a-Chirality of Ketones
Show others...
2017 (English)In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 56, no 16, p. 4535-4539Article in journal (Refereed) Published
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.

Keywords
asymmetric carbocyclization, enallenes, homogeneous catalysis, oxidation, palladium
National Category
Organic Chemistry
Research subject
Organic Chemistry
Identifiers
urn:nbn:se:su:diva-141526 (URN)10.1002/anie.201612385 (DOI)000398154000023 ()
Funder
EU, European Research CouncilSwedish Research CouncilBerzelii Centre EXSELENTKnut and Alice Wallenberg Foundation
Available from: 2017-04-05 Created: 2017-04-05 Last updated: 2022-07-06Bibliographically approved
Qiu, Y., Yang, B., Jiang, T., Zhu, C. & Bäckvall, J.-E. (2017). Palladium-Catalyzed Oxidative Cascade Carbonylative Spirolactonization of Enallenols. Angewandte Chemie International Edition, 56(12), 3221-3225
Open this publication in new window or tab >>Palladium-Catalyzed Oxidative Cascade Carbonylative Spirolactonization of Enallenols
Show others...
2017 (English)In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 56, no 12, p. 3221-3225Article in journal (Refereed) Published
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.

Place, publisher, year, edition, pages
Wiley-VCH Verlagsgesellschaft, 2017
Keywords
carbocyclization, enallenols, oxidation, palladium, spirolactones
National Category
Organic Chemistry
Identifiers
urn:nbn:se:su:diva-142591 (URN)10.1002/anie.201612384 (DOI)000397329300015 ()28211212 (PubMedID)
Funder
EU, European Research CouncilSwedish Research CouncilBerzelii Centre EXSELENTKnut and Alice Wallenberg Foundation
Available from: 2017-05-03 Created: 2017-05-03 Last updated: 2022-02-28Bibliographically approved
Jiang, T., Quan, X., Zhu, C., Andersson, P. G. & Bäckvall, J.-E. (2016). Palladium-Catalyzed Oxidative Synthesis of a-Acetoxylated Enones from Alkynes. Angewandte Chemie International Edition, 55(19), 5824-5828
Open this publication in new window or tab >>Palladium-Catalyzed Oxidative Synthesis of a-Acetoxylated Enones from Alkynes
Show others...
2016 (English)In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 55, no 19, p. 5824-5828Article in journal (Refereed) Published
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.

Place, publisher, year, edition, pages
Wiley-VCH Verlagsgesellschaft, 2016
Keywords
alkynes, enones, oxidation, palladium, sulfoxides
National Category
Organic Chemistry
Identifiers
urn:nbn:se:su:diva-131000 (URN)10.1002/anie.201600696 (DOI)000375118500029 ()27060476 (PubMedID)
Funder
EU, European Research CouncilSwedish Research CouncilBerzelii Centre EXSELENT
Available from: 2016-06-09 Created: 2016-06-09 Last updated: 2022-02-23Bibliographically approved
Zhu, C., Yang, B., Jiang, T. & Bäckvall, J.-E. (2015). Olefin-Directed Palladium-Catalyzed Regio- and Stereoselective Oxidative Arylation of Allenes. Angewandte Chemie International Edition, 54(31), 9066-9069
Open this publication in new window or tab >>Olefin-Directed Palladium-Catalyzed Regio- and Stereoselective Oxidative Arylation of Allenes
2015 (English)In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 54, no 31, p. 9066-9069Article in journal (Refereed) Published
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.

Keywords
allenes, arylation, directing groups, oxidation, palladium
National Category
Organic Chemistry
Research subject
Organic Chemistry
Identifiers
urn:nbn:se:su:diva-120087 (URN)10.1002/anie.201502924 (DOI)000358501500035 ()
Funder
EU, European Research CouncilSwedish Research CouncilBerzelii Centre EXSELENTKnut and Alice Wallenberg Foundation
Available from: 2015-09-07 Created: 2015-09-01 Last updated: 2022-02-23Bibliographically approved
Jiang, T., Bartholomeyzik, T., Mazuela, J., Willersinn, J. & Bäckvall, J.-E. (2015). Palladium(II)/Bronsted Acid-Catalyzed Enantioselective Oxidative Carbocyclization-Borylation of Enallenes. Angewandte Chemie International Edition, 54(20), 6024-6027
Open this publication in new window or tab >>Palladium(II)/Bronsted Acid-Catalyzed Enantioselective Oxidative Carbocyclization-Borylation of Enallenes
Show others...
2015 (English)In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 54, no 20, p. 6024-6027Article in journal (Refereed) Published
Abstract [en]

An enantioselective oxidative carbocyclization-borylation of enallenes that is catalyzed by palladium(II) and a Bronsted acid was developed. Biphenol-type chiral phosphoric acids were superior co-catalysts for inducing the enantioselective cyclization. A number of chiral borylated carbocycles were synthesized in high enantiomeric excess.

Keywords
carbocyclization, chiral anion, chiral phosphoric acid, oxidation, palladium
National Category
Organic Chemistry
Research subject
Organic Chemistry
Identifiers
urn:nbn:se:su:diva-117774 (URN)10.1002/anie.201501048 (DOI)000354255400041 ()
Funder
EU, European Research CouncilSwedish Research CouncilBerzelii Centre EXSELENTKnut and Alice Wallenberg Foundation
Available from: 2015-06-05 Created: 2015-06-01 Last updated: 2022-02-23Bibliographically approved
Jiang, T. (2014). Palladium(II)-Catalyzed Oxidative Carbocyclization: Stereoselective Formation of C–C and C–B Bonds. (Doctoral dissertation). Stockholm: Department of Organic Chemistry, Stockholm University
Open this publication in new window or tab >>Palladium(II)-Catalyzed Oxidative Carbocyclization: Stereoselective Formation of C–C and C–B Bonds
2014 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

Transition metal catalysis has emerged as one of the most versatile methods for the selective formation of carbon–carbon and carbon–heteroatom bonds. In particular, oxidative carbon–carbon bond forming reactions have been widely studied due to their atom economic feature. This thesis has been focused on the development of new palladium(II)-catalyzed carbocyclization reactions under oxidative conditions.

The first part of the thesis describes the palladium(II)-catalyzed oxidative carbocyclization-borylation and -arylation of enallenes. In these reactions, the (σ-alkyl)palladium(II) intermediate, which was shown previously to undergo β-hydride elimination, could be trapped in situ by organoboron reagents (B2pin2 and arylboronic acids) to form new carbon–boron and carbon–carbon bonds. Through these two protocols, a range of borylated and arylated carbocycles were obtained as single diastereomers in high yields.

The second part deals with a palladium(II)-catalyzed oxidative diarylative carbocyclization of enynes. The reaction was proposed to start with a syn-arylpalladation of an alkyne, followed by insertion of the coordinated alkene. Subsequent arylation afforded a series of valuable diarylated tetrahydrofuran and tetrahydropyran products.

The final part of the thesis advances the previously developed palladium(II)-catalyzed oxidative carbocyclization-borylation of enallenes in an enantioselective manner. C2-symmetric chiral phosphoric acids were used as the novel co-catalyst to trigger the enantioselective formation of intramolecular carbon–carbon bonds. By using this chiral anion strategy, a number of enallenes were converted to the borylated carbocycles with high to excellent enantioselectivity.

Place, publisher, year, edition, pages
Stockholm: Department of Organic Chemistry, Stockholm University, 2014. p. 72
Keywords
Carbocyclization, Palladium catalysis, Oxidation, Enallenes, Enynes, Borylation, Arylation, Asymmetric Catalysis, Chiral Brønsted acids, Chiral anion
National Category
Organic Chemistry
Research subject
Organic Chemistry
Identifiers
urn:nbn:se:su:diva-108669 (URN)978-91-7649-020-4 (ISBN)
Public defence
2014-12-05, Magnélisalen, Kemiska övningslaboratoriet, Svante Arrhenius väg 16 B, Stockholm, 14:00 (English)
Opponent
Supervisors
Note

At the time of the doctoral defense, the following paper was unpublished and had a status as follows: Paper 4: Manuscript.

Available from: 2014-11-13 Created: 2014-10-31 Last updated: 2022-02-23Bibliographically approved
Alamsetti, S. K., Persson, A. K. A., Jiang, T. & Bäckvall, J.-E. (2013). Scalable Synthesis of Oxazolones from Propargylic Alcohols through Multistep Palladium(II) Catalysis: beta-Selective Oxidative Heck Coupling of Cyclic Sulfonyl Enamides and Aryl Boroxines. Angewandte Chemie International Edition, 52(51), 13745-13750
Open this publication in new window or tab >>Scalable Synthesis of Oxazolones from Propargylic Alcohols through Multistep Palladium(II) Catalysis: beta-Selective Oxidative Heck Coupling of Cyclic Sulfonyl Enamides and Aryl Boroxines
2013 (English)In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 52, no 51, p. 13745-13750Article in journal (Refereed) Published
Keywords
arylation, boroxines, oxazolones, oxidative Heck coupling, palladium
National Category
Organic Chemistry
Research subject
Organic Chemistry
Identifiers
urn:nbn:se:su:diva-100664 (URN)10.1002/anie.201307471 (DOI)000328437200051 ()
Funder
Swedish Research CouncilEU, European Research Council, 247014
Note

AuthorCount:4;

Available from: 2014-02-12 Created: 2014-02-10 Last updated: 2022-02-24Bibliographically approved
Jiang, M., Jiang, T. & Bäckvall, J.-E. (2012). Palladium-Catalyzed Oxidative Diarylating Carbocyclization of Enynes. Organic Letters, 14(13), 3538-3541
Open this publication in new window or tab >>Palladium-Catalyzed Oxidative Diarylating Carbocyclization of Enynes
2012 (English)In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 14, no 13, p. 3538-3541Article in journal (Refereed) Published
Abstract [en]

A mild and efficient palladium-catalyzed oxidative diarylating carbocyclization of enynes is described. The reaction tolerates a range of functionalized arylboronic acids to give diarylated products in good yields. Control experiments suggest that the reaction starts with an arylpalladation of the alkyne, followed by carbocyclization, transmetalation, and reductive elimination to afford the diarylated product.

National Category
Organic Chemistry
Research subject
Organic Chemistry
Identifiers
urn:nbn:se:su:diva-86241 (URN)10.1021/ol301551x (DOI)000306050300077 ()
Funder
Swedish Research CouncilEU, European Research Council, ERC AdG247014
Available from: 2013-01-11 Created: 2013-01-11 Last updated: 2022-02-24Bibliographically approved
Jiang, T. (2012). Palladium(II)-catalyzed oxidativecarbocyclization: Functionalization with Boron-Containing Reagents. (Licentiate dissertation). Stockholm: Department of Organic Chemistry, Stockholm University
Open this publication in new window or tab >>Palladium(II)-catalyzed oxidativecarbocyclization: Functionalization with Boron-Containing Reagents
2012 (English)Licentiate thesis, comprehensive summary (Other academic)
Place, publisher, year, edition, pages
Stockholm: Department of Organic Chemistry, Stockholm University, 2012. p. 36
National Category
Organic Chemistry
Research subject
Organic Chemistry
Identifiers
urn:nbn:se:su:diva-77067 (URN)
Presentation
2012-06-18, Room A501/507, Svante Arrhenius väg 16 C, Stockholm, 14:00 (English)
Available from: 2012-05-30 Created: 2012-05-30 Last updated: 2022-02-24Bibliographically approved
Persson, A. K. A., Jiang, T., Johnson, M. T. & Bäckvall, J.-E. (2011). Palladium-Catalyzed Oxidative Borylative Carbocyclization of Enallenes. Angewandte Chemie International Edition, 50(27), 6155-6159
Open this publication in new window or tab >>Palladium-Catalyzed Oxidative Borylative Carbocyclization of Enallenes
2011 (English)In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 50, no 27, p. 6155-6159Article in journal (Refereed) Published
Abstract [en]

An efficient oxidative carbocyclization/borylation of enallenes uses Pd(OAc)2 as the catalyst, B2pin2 as the boron-transfer reagent, and 1,4-benzoquinone (BQ) as the oxidant (see scheme). The reaction seems to take place through activation of the allene by a PdII complex to give an alkenyl–PdII intermediate followed by carbopalladation of the olefin and subsequent cleavage of the intermediate palladium–carbon bond by the boron reagent.

Keywords
borylation, carbocyclization, enallenes, oxidation, palladium
National Category
Organic Chemistry
Research subject
Organic Chemistry
Identifiers
urn:nbn:se:su:diva-59546 (URN)10.1002/anie.201008032 (DOI)000292641200030 ()
Funder
EU, European Research CouncilSwedish Research CouncilKnut and Alice Wallenberg Foundation
Available from: 2011-07-05 Created: 2011-07-05 Last updated: 2022-02-24Bibliographically approved
Organisations

Search in DiVA

Show all publications