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  • 1. Belda, O
    et al.
    Kaiser, N F
    Bremberg, U
    Larhed, M
    Hallberg, A
    Moberg, C
    Highly stereo- and regioselective allylations catalyzed by Mo-pyridylamide complexes: Electronic and steric effects of the ligand2000In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 65, no 18, p. 5868-5870Article in journal (Refereed)
  • 2. Bengtson, A
    et al.
    Hallberg, A
    Larhed, M
    Fast synthesis of aryl triflates with controlled microwave heating2002In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 4, no 7, p. 1231-1233Article in journal (Refereed)
    Abstract [en]

    [GRAPHICS] Synthesis of aryl triflates from phenols using N-phenyltriflimide requires only 6 min for completion when conducted with controlled microwave heating. The methodology was applied to both solution- and solid-phase conditions. Ten different aryl triflates were synthesized and isolated in good yields. Applications in high-throughput chemistry are suggested.

  • 3. Bengtson, A
    et al.
    Larhed, M
    Hallberg, A
    Protected indanones by a Heck-Aldol annulation reaction2002In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 67, no 16, p. 5854-5856Article in journal (Refereed)
    Abstract [en]

    Monoprotected 3-hydroxyindan-1-ones have been prepared in moderate to good yields by a new tandem reaction involving salicylaldehyde triflates and commercially available 2-hydroxyethyl vinyl ether. This one-pot annulation reaction proceeds in the presence of a palladium bidentate catalyst and results in the formation of two new ring systems.

  • 4. Bremberg, U
    et al.
    Lutsenko, S
    Kaiser, N F
    Larhed, M
    Hallberg, A
    Mobert, C
    Rapid and stereoselective C-C, C-O, C-N and C-S couplings via microwave accelerated palladium-catalyzed allylic substitutions2000In: Synthesis (Stuttgart), ISSN 0039-7881, E-ISSN 1437-210X, no 7, p. 1004-1008Article in journal (Refereed)
    Abstract [en]

    Palladium-catalyzed substitution of cyclohex-2-en-1-yl ethyl carbonate with neutral C-, O-, and N-nucleophiles was achieved in 1-2 minutes using microwave flash hearing. Enantioselectivities up to 96% were observed. Ionic nucleophiles tended to result in lower ee. With S-nucleophiles problems with the stability of the nucleophile were encountered.

  • 5. Georgsson, J
    et al.
    Hallberg, A
    Larhed, M
    Rapid palladium-catalyzed synthesis of esters from aryl halides utilizing Mo(CO)(6) as a solid carbon monoxide source2003In: Journal of combinatorial chemistry, ISSN 1520-4766, E-ISSN 1520-4774, Vol. 5, no 4, p. 350-352Article in journal (Refereed)
  • 6.
    Johannesson, P
    et al.
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry.
    Lindeberg, G
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry.
    Tong, W
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry.
    Gogoll, Adolf
    Synnergren, B
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Pharmaceutical Biosciences.
    Nyberg, F
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Pharmaceutical Biosciences.
    Karlen, A
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry.
    Hallberg, A
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry.
    Angiotensin II analogues encompassing 5,9- and 5,10-fusedthiazabicycloalkane tripeptide mimetics.1999In: Journal of Medicinal Chemistry, ISSN 0022-2623, E-ISSN 1520-4804, Vol. 42, p. 4524-4537Article in journal (Refereed)
  • 7.
    Johannesson, P
    et al.
    Uppsala University.
    Lindeberg, G
    Uppsala University.
    Tong, WM
    Uppsala University.
    Gogoll, Adolf
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry.
    Synnergren, B
    Uppsala University.
    Nyberg, F
    Uppsala University.
    Karlen, A
    Uppsala University.
    Hallberg, A
    Uppsala University.
    Angiotensin II analogues encompassing 5,9-and 5,10-fused thiabicycloalkane tripeptide mimetics1999In: Journal of Medicinal Chemistry, ISSN 0022-2623, E-ISSN 1520-4804, Vol. 42, no 22, p. 4524-4537p. 4524-4537Article in journal (Refereed)
    Abstract [en]

    A simple experimental procedure on solid phase for the construction of new tripeptidic 5,9- and 5,10-fused thiazabicycloalkane scaffolds that adopt beta-turns has been developed. This N-terminal-directed bicyclization, relying on masked aldehyde precurso

  • 8. Kaiser, N F K
    et al.
    Bremberg, U
    Larhed, M
    Moberg, C
    Hallberg, A
    Fast, convenient, and efficient molybdenum-catalyzed asymmetric allylic alkylation under noninert conditions: An example of microwave-promoted fast chemistry2000In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 39, no 20, p. 3596-3598Article in journal (Refereed)
  • 9. Kaiser, N F K
    et al.
    Bremberg, U
    Larhed, M
    Moberg, C
    Hallberg, A
    Microwave-mediated palladium-catalyzed asymmetric allylic alkylation; an example of highly selective fast chemistry2000In: Journal of Organometallic Chemistry, ISSN 0022-328X, E-ISSN 1872-8561, Vol. 603, no 1, p. 2-5Article in journal (Refereed)
    Abstract [en]

    Highly enantioselective palladium-catalyzed microwave-mediated fast chemistry has been performed on dimethyl malonate alkylation of(rac)-1,3-diphenylallyl-1-acetate (1). Utilizing the recently developed palladium-phosphineoxazoline catalytic system, with general stability at elevated temperatures (less than or equal to 145 degrees C), quantitative yields of greater than or equal to 97% and ee values of up to >99% were obtained after very short irradiation times (15-300 s, TOF up to 7000 h(-1)). (C) 2000 Elsevier Science S.A. All rights reserved.

  • 10. Kaiser, N F K
    et al.
    Hallberg, A
    Larhed, M
    In situ generation of carbon monoxide from solid molybdenum hexacarbonyl. A convenient and fast route to palladium-catalyzed carbonylation reactions2002In: Journal of combinatorial chemistry, ISSN 1520-4766, E-ISSN 1520-4774, Vol. 4, no 2, p. 109-111Article in journal (Refereed)
  • 11. Larhed, M
    et al.
    Hallberg, A
    Microwave-assisted high-speed chemistry: a new technique in drug discovery2001In: Drug Discovery Today, ISSN 1359-6446, E-ISSN 1878-5832, Vol. 6, no 8, p. 406-416Article, review/survey (Refereed)
    Abstract [en]

    In both lead identification and lead optimization processes there is an acute need for new organic small molecules. Traditional methods of organic synthesis are orders of magnitude too slow to satisfy the demand for these compounds. The fields of combinatorial and automated medicinal chemistry have been developed to meet the increasing requirement of new compounds for drug discovery; within these fields, speed is of the essence. The efficiency of microwave flash-heating chemistry in dramatically reducing reaction times (reduced from days and hours to minutes and seconds) has recently been proven in several different fields of organic chemistry. We believe that the time saved by using focused microwaves is potentially important in traditional organic synthesis but could be of even greater importance in high-speed combinatorial and medicinal chemistry.

  • 12. Larhed, M
    et al.
    Moberg, C
    Hallberg, A
    Microwave-accelerated homogeneous catalysis in organic chemistry2002In: Accounts of Chemical Research, ISSN 0001-4842, E-ISSN 1520-4898, Vol. 35, no 9, p. 717-727Article, review/survey (Refereed)
    Abstract [en]

    The efficiency of microwave flash heating in accelerating organic transformations (reaction times reduced from days and hours to minutes and seconds) has recently-been proven in several different fields of organic chemistry. This specific account mainly summarizes our own experiences in developing rapid, robust, and selective microwave-assisted transition metal-catalyzed homogeneous reactions. Applications include selective Heck couplings, cross-couplings, and asymmetric substitutions. The science of green chemistry was developed to meet the increasing demand for environmentally benign chemical processes. We believe the combination of metal catalysis and microwave heating will be of importance in the search for green laboratory-scale synthesis.

  • 13. Nilsson, P
    et al.
    Gold, H
    Larhed, M
    Hallberg, A
    Microwave-assisted enantioselective Heck reactions: Expediting high reaction speed and preparative convenience2002In: Synthesis (Stuttgart), ISSN 0039-7881, E-ISSN 1437-210X, no 11, p. 1611-1614Article in journal (Refereed)
    Abstract [en]

    Palladium-catalyzed asymmetric Heck reactions have been per-formed using high temperature conditions with the aid of controlled microwave dielectric heating. Significant enantioselectivities of up to 92% ee were obtained under non-inert conditions utilizing the previously reported thermostable palladium-phosphineoxazoline catalytic system. With microwave irradiation. reaction times of hours instead of days were obtained. Enantiomeric purities and conversions were found to be strongly dependent on both the choice of the aryl triflate, the reaction temperature, the solvent and the base. Examples of asymmetric arylations of electron-rich as well as neutral cyclic alkenes are presented.

  • 14. Nilsson, P
    et al.
    Larhed, M
    Hallberg, A
    A new highly asymmetric chelation-controlled heck arylation2003In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 125, no 12, p. 3430-3431Article in journal (Refereed)
  • 15. Nilsson, P
    et al.
    Larhed, M
    Hallberg, A
    Highly regioselective, sequential, and multiple palladium-catalyzed arylations of vinyl ethers carrying a coordinating auxiliary: An example of a Heck triarylation process2001In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 123, no 34, p. 8217-8225Article in journal (Refereed)
    Abstract [en]

    This article describes the development of new auxiliary-accelerated Heck multiarylations by intramolecular presentation of the oxidative addition complex. The introduction of a specific, palladium-coordinating dimethylamino group allows for the desired chelation-accelerated and chelation-controlled triand diarylation reactions. We report (a) the first example of a Heck triarylation process, (b) highly selective palladium-catalyzed diarylations of alkyl vinyl ethers, and (c) a very rapid two-phase protocol for the microwave-assisted hydrolysis of amino-substituted, arylated vinyl ethers constituting an entry to diarylated ethanals and substituted desoxybenzoins. X-ray structures and product patterns support the suggested substrate-controlled Heck reaction pathway. The catalyst-directing alkyl dimethylamino functionality was rapidly (1-2 min) and efficiently released by microwave hydrolysis after Heck multiarylation reactions. The liberated aromatic carbonyl compounds were thereafter isolated and fully characterized.

  • 16. Olofsson, K
    et al.
    Larhed, M
    Hallberg, A
    Highly regioselective palladium-catalyzed beta-arylation of N,N-dialkylallylamines2000In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 65, no 21, p. 7235-7239Article in journal (Refereed)
  • 17. Olofsson, K
    et al.
    Larhed, M
    Hallberg, A
    Highly regioselective palladium-catalyzed internal arylation of allyltrimethylsilane with aryl triflates1998In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 63, no 15, p. 5076-5079Article in journal (Refereed)
    Abstract [en]

    Highly regioselective ligand-controlled Heck-arylation reactions of allyltrimethylsilane, delivering branched beta-products, were performed in moderate to good yields. The high preference for internal over terminal double-bond arylation suggests a contribution from the beta-cation-stabilizing effect of silicon. Microwave-promoted palladium-catalyzed coupling reactions proceeded with the same regioselectivity in six entries out of eight with the reaction times cut sharply down to 5-10 min.

  • 18. Olofsson, K
    et al.
    Sahlin, H
    Larhed, M
    Hallberg, A
    Regioselective palladium-catalyzed synthesis of beta-arylated primary allylamine equivalents by an efficient Pd-N coordination2001In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 66, no 2, p. 544-549Article in journal (Refereed)
    Abstract [en]

    A highly regioselective Heck arylation, utilizing aryl triflates and a palladium/dppf catalytic system, can be performed at the internal, beta -carbon of Boc- and phthalimido-protected allylamines, yielding arylated primary allylamine equivalents. The very high regioselectivity obtained with secondary Boc-protected allylamides is suggested to be caused by an efficient coordination between an anionic nitrogen and palladium. Single-mode microwave irradiation has been utilized to shorten the reaction times and, in the case of Boc-protected allylamides, to improve the yields of two electron-poor aryl triflates.

  • 19. Vallin, K S A
    et al.
    Emilsson, P
    Larhed, M
    Hallberg, A
    High-speed Heck reactions in ionic liquid with controlled microwave heating2002In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 67, no 17, p. 6243-6246Article in journal (Refereed)
    Abstract [en]

    Palladium-catalyzed Heck arylations in the polar and robust ionic liquid, 1-butyl-3-methylimidazolium hexafluorophosphate (bmimPF(6)), have for the first time been accomplished under microwave irradiation. The couplings were efficiently performed in sealed tubes within 5-45 min of heating. Without significant reductions in yield, a phosphine-free ionic catalyst phase could be recycled in five successive 20 min reactions at 180 degreesC. The product was easily removed from the reaction medium by distillation.

  • 20. Vallin, K S A
    et al.
    Larhed, M
    Hallberg, A
    Aqueous DMF-potassium carbonate as a substitute for thallium and silver additives in the palladium-catalyzed conversion of aryl bromides to acetyl arenes2001In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 66, no 12, p. 4340-4343Article in journal (Refereed)
    Abstract [en]

    Highly selective palladium-catalyzed internal alpha -arylations of alkyl vinyl ethers with aryl and heteroaryl bromides were conveniently conducted in aqueous DMF with potassium carbonate as base and with DPPP as bidentate ligand. The corresponding acetyl arene products were, after hydrolysis, isolated in good to excellent yields. This Heck reaction procedure does not require toxic thallium or expensive silver salt additives, is promoted by water, and is suggested to proceed via charged organopalladium intermediates. Single-mode microwave irradiation was utilized in one example to shorten the reaction time.

  • 21. Vallin, K S A
    et al.
    Larhed, M
    Johansson, K
    Hallberg, A
    Highly selective palladium-catalyzed synthesis of protected alpha,beta-unsaturated methyl ketones and 2-alkoxy-1,3-butadienes. High-speed chemistry by microwave flash heating2000In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 65, no 15, p. 4537-4542Article in journal (Refereed)
    Abstract [en]

    A selective and mild procedure is described for the direct synthesis of 2-alkene-2-methyl-1,3-dioxolanes via regiocontrolled Heck vinylation of commercially available 2-hydroxyethyl vinyl ether. The procedure permits chemoselective transformation of a vinylic triflate or bromide into a blocked alpha,beta-unsaturated methyl ketone. Furthermore, a significantly improved and highly regioselective synthesis of 2-alkoxy-1,3-butadienes has been developed. Flash heating by microwave irradiation promotes the palladium-catalyzed reactions, and the starting materials are fully converted after reaction times of 5-7 min.

  • 22. Vallin, K S A
    et al.
    Zhang, Q S
    Larhed, M
    Curran, D P
    Hallberg, A
    A new regioselective Heck vinylation with enamides. Synthesis and investigation of fluorous-tagged bidentate ligands for fast separation2003In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 68, no 17, p. 6639-6645Article in journal (Refereed)
    Abstract [en]

    Internal ligand-controlled Heck vinylations of enamides were performed with high regioselectivity and delivered moderate to good yields of dienamides. Controlled heating by microwave irradiation accelerated the palladium-catalyzed reactions, and full conversions were achieved after reaction times of only 15-30 min. New bidentate fluorous-tagged 1,3-bis(diphenylphosphino)propane ligands (F-dppp's) were synthesized and examined. The cationic vinylations of the enamides with F-dppp ligands rendered essentially the same alpha-selectivity and catalytic activity as in those vinylations where nonfluorous ligands were employed. After reaction, the fluorous-tagged ligand material was easily removed by convenient solid fluorous phase separation. The high selectivity, simplicity, and generality of the experimental procedure should make this approach to 2-acylamino-1,3-butadienes attractive.

  • 23. Wan, Y Q
    et al.
    Alterman, M
    Larhed, M
    Hallberg, A
    Dimethylformamide as a carbon monoxide source in fast palladium-catalyzed aminocarbonylations of aryl bromides2002In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 67, no 17, p. 6232-6235Article in journal (Refereed)
    Abstract [en]

    Dimethylformamide (DMF) acts as an efficient source of carbon monoxide and dimethylamine in the palladium-catalyzed aminocarbonylation (Heck carbonylation) of p-tolyl bromide to provide the dimethylamide. Addition of amines to the reaction mixture in excess delivers the corresponding aryl amides in good yields. The amines employed, benzylamine, morpholine, and aniline, all constitute good reaction partners. The reaction proceeds smoothly with bromobenzene and more electron-rich aryl bromides, but electron-deficient aryl bromides fail to undergo aminocarbonylation. The reactions are conducted at 180-190 degreesC for 15-20 min with microwave heating in a reaction mixture containing imidazole and potassium tert-butoxide: the latter is required to promote decomposition of the DMF solvent at a suitable rate. The beneficial effects of controlled microwave irradiation as an energy source for the rapid heating of the carbonylation reaction mixture are demonstrated. The carbonylation procedure reported herein, which relies on the in situ generation of carbon monoxide, serves as a convenient alternative to other carbonylation methods and is particularly applicable to small-scale reactions where short reaction times are desired and the direct use of carbon monoxide gas is impractical.

  • 24. Wan, Y Q
    et al.
    Alterman, M
    Larhed, M
    Hallberg, A
    Formamide as a combined ammonia synthon and carbon monoxide source in fast palladium-catalyzed aminocarbonylations of aryl halides2003In: Journal of combinatorial chemistry, ISSN 1520-4766, E-ISSN 1520-4774, Vol. 5, no 2, p. 82-84Article in journal (Refereed)
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