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Search for "Heck" in Full Text gives 168 result(s) in Beilstein Journal of Organic Chemistry.

Synthesis of 3-alkenylindoles through regioselective C–H alkenylation of indoles by a ruthenium nanocatalyst

  • Abhijit Paul,
  • Debnath Chatterjee,
  • Srirupa Banerjee and
  • Somnath Yadav

Beilstein J. Org. Chem. 2020, 16, 140–148, doi:10.3762/bjoc.16.16

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  • Pd-catalysed Fujiwara–Moritani or oxidative dehydrogenative Heck reaction via dual C–H activation [21][22][23][24]. One of the early examples of this reaction, reported by Gaunt and co-workers, involved the regioselective, solvent-controlled C3 alkenylation of indoles with alkenes containing electron
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Published 29 Jan 2020

Functionalization of the imidazo[1,2-a]pyridine ring in α-phosphonoacrylates and α-phosphonopropionates via microwave-assisted Mizoroki–Heck reaction

  • Damian Kusy,
  • Agata Wojciechowska,
  • Joanna Małolepsza and
  • Katarzyna M. Błażewska

Beilstein J. Org. Chem. 2020, 16, 15–21, doi:10.3762/bjoc.16.3

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  • ]pyridine ring has been synthesized via the microwave-assisted Mizoroki–Heck reaction. The efficient modification of the imidazo[1,2-a]pyridine ring has been achieved as late-stage functionalization, enabling and accelerating the generation of a library of compounds from a common precursor. Keywords: α
  • -phosphonoacrylates; α-phosphonopropionates; imidazo[1,2-a]pyridine; microwave-assisted reaction; Mizoroki–Heck reaction; Introduction In the last few decades, the Mizoroki–Heck reaction has become one of the main tools in organic synthesis. Its use for the functionalization of a wide range of compounds cannot be
  • confirmed by the presence in a number of pharmaceuticals [2][3]. The imidazo[1,2-a]pyridine-ring modification via Pd-catalyzed reactions is broadly reported in the literature [3], however, such functionalizations for more complex molecules are not very common. On the other hand, the Mizoroki–Heck reaction
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Published 03 Jan 2020

Functionalization of 4-bromobenzo[c][2,7]naphthyridine via regioselective direct ring metalation. A novel approach to analogues of pyridoacridine alkaloids

  • Benedikt C. Melzer,
  • Alois Plodek and
  • Franz Bracher

Beilstein J. Org. Chem. 2019, 15, 2304–2310, doi:10.3762/bjoc.15.222

Graphical Abstract
  • synthesis via an Heck-type palladium-catalysed reaction according to the method of Harayama [30] (Pd(II)acetate/tri(o-tolyl)phosphine/K2CO3) did not lead to the expected alkaloid 3. Also the radical procedure published by Markgraf et al. [31] using AIBN and Bu3SnH and a photochemical cyclization protocol we
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Published 26 Sep 2019

Recent advances in transition-metal-catalyzed incorporation of fluorine-containing groups

  • Xiaowei Li,
  • Xiaolin Shi,
  • Xiangqian Li and
  • Dayong Shi

Beilstein J. Org. Chem. 2019, 15, 2213–2270, doi:10.3762/bjoc.15.218

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Published 23 Sep 2019

Azologization and repurposing of a hetero-stilbene-based kinase inhibitor: towards the design of photoswitchable sirtuin inhibitors

  • Christoph W. Grathwol,
  • Nathalie Wössner,
  • Sören Swyter,
  • Adam C. Smith,
  • Enrico Tapavicza,
  • Robert K. Hofstetter,
  • Anja Bodtke,
  • Manfred Jung and
  • Andreas Link

Beilstein J. Org. Chem. 2019, 15, 2170–2183, doi:10.3762/bjoc.15.214

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  • available naphthalene-2-ylboronic acid or (3,4-dihydronaphthalen-2-yl)boronic acid (Scheme 1). The latter was synthesized according to a literature procedure [36]. Formation of compounds 2b–h was accomplished through Heck coupling of aryl bromides with the appropriate styrenes (Scheme 2) [37]. Compounds 2b
  • and 2e were obtained in moderate yield using 3a as the aryl halide in the Heck reaction. The use of 3b in the Heck reaction resulted in a substantial improvement of yield in the synthesis of 2g but not for 2c. Interchanging the roles by using 5-vinylnicotinamide (5a) or methyl 5-vinylnicotinate (5b
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Published 16 Sep 2019

Recent advances on the transition-metal-catalyzed synthesis of imidazopyridines: an updated coverage

  • Gagandeep Kour Reen,
  • Ashok Kumar and
  • Pratibha Sharma

Beilstein J. Org. Chem. 2019, 15, 1612–1704, doi:10.3762/bjoc.15.165

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  • Suzuki, Sonogashira and Heck coupling reactions (Scheme 48). The reaction proceeded by the formation of 1-iodoalkyne 142 which was characterized by mass and 1H NMR spetra. This iodoalkyne then formed a complex of Cu(I) with 2-AP. This was followed by migratory insertion of haloalkyne to form reactive Cu
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Published 19 Jul 2019

Multicomponent reactions (MCRs): a useful access to the synthesis of benzo-fused γ-lactams

  • Edorta Martínez de Marigorta,
  • Jesús M. de Los Santos,
  • Ana M. Ochoa de Retana,
  • Javier Vicario and
  • Francisco Palacios

Beilstein J. Org. Chem. 2019, 15, 1065–1085, doi:10.3762/bjoc.15.104

Graphical Abstract
  • comprising three palladium-catalysed reactions: Sonogashira, Heck and Suzuki–Miyaura (Scheme 37) [113][114][115]. In this methodology, N-arylpropiolamides 128 reacted with aryl iodides 129 and aryl- or styrylboronic acids 130 under microwave activation to yield 3-(diarylmethylene)oxindoles 131 or 3-(1,3
  • Heck cyclization reaction between the substituted alkyne and aryl bromide in 133 takes place to form a cyclic palladium intermediate 134 with E-configuration, resulting from a syn-addition mechanism of this step. The addition of a silver salt reduces the probability of isomerization of the double bond
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Published 08 May 2019

Heck- and Suzuki-coupling approaches to novel hydroquinone inhibitors of calcium ATPase

  • Robert J. Kempton,
  • Taylor A. Kidd-Kautz,
  • Soizic Laurenceau and
  • Stefan Paula

Beilstein J. Org. Chem. 2019, 15, 971–975, doi:10.3762/bjoc.15.94

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  • Abstract In this study, we explored Heck- and Suzuki-coupling methodology to modify the template 2,5-di-tert-butylhydroquinone (BHQ, 2), an inhibitor of the enzyme sarco/endoplasmic reticulum calcium ATPase (SERCA). We found that by utilizing Suzuki coupling, we could successfully attach a six-carbon
  • convey specificity for prostate cancer cells. Keywords: calcium ATPase inhibitors; Heck- and Suzuki-coupling reactions; hydroquinones; prostate cancer; tethered amino acid; Introduction Sarco/endoplasmic reticulum calcium ATPase (SERCA) is an integral protein that resides in the membrane of the
  • at C-8 of TG, replacing the natural butanoyl group at that position with an ester moiety terminating in a primary amine. Here, we describe our efforts to use transition metal cross-coupling reactions (Suzuki [10] and Heck [11]) to modify BHQ with a side chain terminating with a free primary amine
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Published 24 Apr 2019

The LANCA three-component reaction to highly substituted β-ketoenamides – versatile intermediates for the synthesis of functionalized pyridine, pyrimidine, oxazole and quinoxaline derivatives

  • Tilman Lechel,
  • Roopender Kumar,
  • Mrinal K. Bera,
  • Reinhold Zimmer and
  • Hans-Ulrich Reissig

Beilstein J. Org. Chem. 2019, 15, 655–678, doi:10.3762/bjoc.15.61

Graphical Abstract
  • . The reduction of OX7 followed by elimination to OX21 proceeded smoothly and as subsequent transformation a Heck reaction with alkenyl nonaflate 10 was performed delivering OX22. The conversion of OX7 to alkyne OX23 applied the protocol of Lyapkalo et al. [59] using Schwesinger’s base [60] as crucial
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Published 13 Mar 2019

Application of olefin metathesis in the synthesis of functionalized polyhedral oligomeric silsesquioxanes (POSS) and POSS-containing polymeric materials

  • Patrycja Żak and
  • Cezary Pietraszuk

Beilstein J. Org. Chem. 2019, 15, 310–332, doi:10.3762/bjoc.15.28

Graphical Abstract
  • chemistry), POSS are often functionalized through the chemical processes of C=C bond transformation, e.g., hydrosilylation, Heck coupling, silylative coupling and olefin metathesis. Olefin metathesis, i.e., catalytic exchange of double bonds between carbon atoms, is a powerful tool in organic synthesis. The
  • subsequently modified via Heck coupling with a set of 4-substituted styrenes to give the next generation of functionalized derivatives. The authors also demonstrated the possibility of further functionalization of an amino-substituted derivative via the reaction with 3,5-dibromo or dinitrobenzoyl chloride. The
  • of vinylsilanes (Scheme 1). The possibility to modify vinyl and styryl derivatives of silsesquioxanes via Heck reaction has been proved. The Heck coupling of 4-bromostyrene and vinyl-POSS derivatives leads to the formation of oligomeric products containing a silsesquioxane core in the polymer
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Published 04 Feb 2019

Gold-catalyzed post-Ugi alkyne hydroarylation for the synthesis of 2-quinolones

  • Xiaochen Du,
  • Jianjun Huang,
  • Anton A. Nechaev,
  • Ruwei Yao,
  • Jing Gong,
  • Erik V. Van der Eycken,
  • Olga P. Pereshivko and
  • Vsevolod A. Peshkov

Beilstein J. Org. Chem. 2018, 14, 2572–2579, doi:10.3762/bjoc.14.234

Graphical Abstract
  • synthesis of 2-quinolones using either intramolecular Heck reaction [60] or Knoevenagel condensation [61][62]. Results and Discussion We began our study with the preparation of the model substrate 7a through the Ugi reaction of tetrolic acid (3a), benzaldehyde (4a), tert-butyl isocyanide (5a) and 3,5
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Published 04 Oct 2018

Hydroarylations by cobalt-catalyzed C–H activation

  • Rajagopal Santhoshkumar and
  • Chien-Hong Cheng

Beilstein J. Org. Chem. 2018, 14, 2266–2288, doi:10.3762/bjoc.14.202

Graphical Abstract
  • (hydroarylation) is a 100% atom economical process to build fundamental alkyls and alkenes (Scheme 2) [42][43][44][45]. It is an efficient alternative to C–H alkylation reactions with alkyl halides where one equivalent of salt waste was released, and dehydrogenative Heck coupling with alkenes for the synthesis of
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Published 29 Aug 2018

Cobalt-catalyzed nucleophilic addition of the allylic C(sp3)–H bond of simple alkenes to ketones

  • Tsuyoshi Mita,
  • Masashi Uchiyama,
  • Kenichi Michigami and
  • Yoshihiro Sato

Beilstein J. Org. Chem. 2018, 14, 2012–2017, doi:10.3762/bjoc.14.176

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  • involving catalytic C–C bond construction with the double bond of terminal alkenes (e.g., Heck reaction, hydrometalation followed by functionalization, carbometalation, and olefin metathesis) [10][11][12][13]. However, direct C–C bond formation of the allylic C(sp3)–H bond adjacent to double bonds has
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Published 02 Aug 2018

Hypervalent organoiodine compounds: from reagents to valuable building blocks in synthesis

  • Gwendal Grelier,
  • Benjamin Darses and
  • Philippe Dauban

Beilstein J. Org. Chem. 2018, 14, 1508–1528, doi:10.3762/bjoc.14.128

Graphical Abstract
  • catalytic domino reactions. The group of Hayashi has reported in 2004 the first example of the transformation of a cyclic diaryl-λ3-iodane, for which both Ar–I bonds are used in a palladium cross-coupling reaction [56]. It relies on a double Heck reaction performed with methyl vinyl ketone in the presence
  • –I motif (Scheme 22) [62]. Hence aryl- and alkyl-substituted terminal alkynes can be coupled via a Sonogashira reaction when PPh3 is used as ligand, while the use of diphenylphosphinoferrocenyl ligand (dppf) allows the Heck-type coupling of acrylates, vinyl ketones and electron-poor styrene
  • , gives access to various iodoaminated intermediates that can be subsequently engaged in palladium-catalyzed Suzuki–Miyaura, Sonogashira, or Mizoroki–Heck cross-coupling reactions. Various aryl, alkenyl, or alkynyl substituents can thus be introduced in good to very good yields. When compared to the
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Published 21 Jun 2018

Atom-economical group-transfer reactions with hypervalent iodine compounds

  • Andreas Boelke,
  • Peter Finkbeiner and
  • Boris J. Nachtsheim

Beilstein J. Org. Chem. 2018, 14, 1263–1280, doi:10.3762/bjoc.14.108

Graphical Abstract
  • iodoarenes 32. These species smoothly underwent subsequent Suzuki–Miyaura, Sonogashira and Mirozoki–Heck couplings. The respective arylated, alkynylated and alkenylated products 33a–d were obtained in high yields with excellent stereoselectivity. Due to the intramolecular pathway of the first step, high AE
  • values (66% for 33b) are obtained. In another tandem procedure, a metal-free C(sp3)–H olefination of amidines 34 with DMSO and PIDA derivatives 20b was developed by Namitharan and co-workers [49]. A Pd(II)-catalysed Heck reaction of the formed exocyclic double bond with the emerging iodoarene yields
  • then oxidized to the sulfoxide G by iodosoarene C via the postulated activated sulfoxide F, releasing one equivalent of aryl iodide 2. A Chugaev-type elimination yields the olefin H, which finally affords acrylamidine 35 via Heck coupling with the iodoarene 2 with 50% AE (for R1 = H, R2 = Bn, Ar1 = Ar2
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Published 30 May 2018

One hundred years of benzotropone chemistry

  • Arif Dastan,
  • Haydar Kilic and
  • Nurullah Saracoglu

Beilstein J. Org. Chem. 2018, 14, 1120–1180, doi:10.3762/bjoc.14.98

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  • benzotropylium ion 45. Secondly, 11 is obtained in 18% yield after benzylic bromination of 42 with NBS, followed by in situ elimination reaction of the labile bromide 43 mediated by t-BuOK (Scheme 9). Palladium-catalyzed C–C bond-formation reactions such as Heck and Sonogashira couplings are employed in a wide
  • variety of areas in organic chemistry [56][57]. Recently, Shaabani’s group synthesized and characterized palladium nanoparticles supported on ethylenediamine-functionalized cellulose (PdNPs@EDACs) as a novel bio-supported catalyst for Heck and Sonogashira couplings in water [58]. Shaabani’s group reported
  • the efficient synthesis of benzotropone 11 in a good isolated yield (83%) via PdNPs@EDACs-catalyzed Heck coupling and intramolecular condensation of 2-bromobenzaldehyde (46) and methyl vinyl ketone (47) (Scheme 10) [58]. 2.2. Reactions of 4,5-benzotropone (11) 2.2.1. Reactions via the carbonyl group
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Published 23 May 2018

Bromide-assisted chemoselective Heck reaction of 3-bromoindazoles under high-speed ball-milling conditions: synthesis of axitinib

  • Jingbo Yu,
  • Zikun Hong,
  • Xinjie Yang,
  • Yu Jiang,
  • Zhijiang Jiang and
  • Weike Su

Beilstein J. Org. Chem. 2018, 14, 786–795, doi:10.3762/bjoc.14.66

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  • , PR China 10.3762/bjoc.14.66 Abstract A mechanically-activated chemoselective Heck coupling for the synthesis of 3-vinylindazoles has been developed with the aid of catalytic amounts of TBAB and NaBr as both dehalogenation restrainer and grinding auxiliary. After tuning of the chemical conditions and
  • mechanical parameters, a series of non-activated 3-bromoindazoles and a broad scope of olefins worked well to give the corresponding coupling products in good to excellent yields. A further application of this protocol was performed in a two-step mechanochemical Heck/Migita cross coupling, which provided a
  • highly efficient route for the synthesis of axitinib. Keywords: axitinib; ball-milling; dehalogenation; Heck reaction; indazoles; Introduction The palladium-catalyzed vinylation of alkenes in the presence of a base, known as the Heck reaction (Mizoroki–Heck reaction), is one of the most important
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Published 06 Apr 2018

Nanoreactors for green catalysis

  • M. Teresa De Martino,
  • Loai K. E. A. Abdelmohsen,
  • Floris P. J. T. Rutjes and
  • Jan C. M. van Hest

Beilstein J. Org. Chem. 2018, 14, 716–733, doi:10.3762/bjoc.14.61

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  • hydrophobic membrane and as a consequence a higher reaction rate. Dergunov et al. reported on the design of a porous polymeric nanoreactor with a lipid bilayer for coupling reactions [87]. These nanocapsules were loaded with palladium catalysts and successfully used in Suzuki, Sonogashira and Heck cross
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Published 29 Mar 2018

Cobalt-catalyzed directed C–H alkenylation of pivalophenone N–H imine with alkenyl phosphates

  • Wengang Xu and
  • Naohiko Yoshikai

Beilstein J. Org. Chem. 2018, 14, 709–715, doi:10.3762/bjoc.14.60

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  • groups into the ortho position of functionalized arenes has attracted significant attention because of the synthetic versatility of alkenyl groups. The C–H alkenylation has been achieved most extensively by way of the dehydrogenative Heck-type reaction of olefins [7][8][9]. Meanwhile, the hydroarylation
  • of alkynes has also been explored as an alternative approach for C–H alkenylation [10]. Despite the significant progress made, each of these C–H alkenylation manifolds has some critical limitations. For example, the dehydrogenative Heck reaction is often limited to activated monosubstituted alkenes
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Published 28 Mar 2018

Diastereoselective auxiliary- and catalyst-controlled intramolecular aza-Michael reaction for the elaboration of enantioenriched 3-substituted isoindolinones. Application to the synthesis of a new pazinaclone analogue

  • Romain Sallio,
  • Stéphane Lebrun,
  • Frédéric Capet,
  • Francine Agbossou-Niedercorn,
  • Christophe Michon and
  • Eric Deniau

Beilstein J. Org. Chem. 2018, 14, 593–602, doi:10.3762/bjoc.14.46

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  • two steps sequence involving first a palladium-catalyzed Heck cross coupling between 2-bromobenzoic tert-butyl esters 9 and 10 with acrylamides 11a–e (69–72% isolated yields, Scheme 2, Figure 2). The subsequent removal of the t-butyl group in esters 12a–e and 13 (Figure 2) was then achieved by
  • Scheme 5. Aldehyde 23 was first readily prepared via a Heck cross coupling reaction between 2-bromobenzaldehyde (22) and acrylamide 11f. Next, a Pinnick oxidation of the aldehyde 23 followed with a coupling reaction with chiral benzylamine 17 delivered the targeted benzamide 24 in good yield (65%). The
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Published 09 Mar 2018

5-Aminopyrazole as precursor in design and synthesis of fused pyrazoloazines

  • Ranjana Aggarwal and
  • Suresh Kumar

Beilstein J. Org. Chem. 2018, 14, 203–242, doi:10.3762/bjoc.14.15

Graphical Abstract
  • ]pyridines 32 and 34 (Scheme 5). In situ cyclocondensation of β-halovinyl aldehydes 29 with 5-aminopyrazoles (R = Ph, 16) under Heck conditions in the presence of Pd(OAc)2 with xantphos (4,5-bis(diphenylphosphino)-9,9-dimethylxanthene) gave 6-substituted pyrazolo[3,4-b]pyridines 34. On the other hand
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Published 25 Jan 2018

Progress in copper-catalyzed trifluoromethylation

  • Guan-bao Li,
  • Chao Zhang,
  • Chun Song and
  • Yu-dao Ma

Beilstein J. Org. Chem. 2018, 14, 155–181, doi:10.3762/bjoc.14.11

Graphical Abstract
  • different functional groups. But the reaction was sensitive to the steric hindrance of the olefin substrates, and 2-substituted terminal alkenes or internal (including cyclic) alkenes were not applicable to this protocol. A mechanistic study showed that the reaction may proceed through a Heck-like four
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Published 17 Jan 2018

CF3SO2X (X = Na, Cl) as reagents for trifluoromethylation, trifluoromethylsulfenyl-, -sulfinyl- and -sulfonylation and chlorination. Part 2: Use of CF3SO2Cl

  • Hélène Chachignon,
  • Hélène Guyon and
  • Dominique Cahard

Beilstein J. Org. Chem. 2017, 13, 2800–2818, doi:10.3762/bjoc.13.273

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  • (CF3SO2)2Zn, which demonstrated great efficiency in introducing the CF3 moiety on (hetero)aromatic rings [34]. Trifluoromethylation of olefins: In 2005, Vogel and co-workers showed that terminal alkenes could be trifluoromethylated by means of CF3SO2Cl via a palladium-catalysed desulfitative Mizoroki–Heck
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Published 19 Dec 2017

Palladium-catalyzed Heck-type reaction of secondary trifluoromethylated alkyl bromides

  • Tao Fan,
  • Wei-Dong Meng and
  • Xingang Zhang

Beilstein J. Org. Chem. 2017, 13, 2610–2616, doi:10.3762/bjoc.13.258

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  • , Shanghai 200032, China 10.3762/bjoc.13.258 Abstract An efficient palladium-catalyzed Heck-type reaction of secondary trifluoromethylated alkyl bromides has been developed. The reaction proceeds under mild reaction conditions with high efficiency and excellent functional group tolerance, even towards
  • formyl and hydroxy groups. Preliminary mechanistic studies reveal that a secondary trifluoromethylated alkyl radical is involved in the reaction. Keywords: alkenes; cross-coupling; Heck-type reaction; palladium; secondary trifluoromethylated alkyl bromides; Introduction With the increasing number of
  • fluoroalkyl metal species [18][19][20][21][22][23][24]. Recently, we reported a palladium-catalyzed Heck-type reaction of fluoroalkyl bromides, representing an efficient and straightforward alternative to access fluoroalkylated alkenes [25][26][27]. Preliminary mechanistic studies reveal that a fluoroalkyl
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Published 06 Dec 2017

Synthesis of substituted Z-styrenes by Hiyama-type coupling of oxasilacycloalkenes: application to the synthesis of a 1-benzoxocane

  • James R. Vyvyan,
  • Courtney A. Engles,
  • Scott L. Bray,
  • Erik D. Wold,
  • Christopher L. Porter and
  • Mikhail O. Konev

Beilstein J. Org. Chem. 2017, 13, 2122–2127, doi:10.3762/bjoc.13.209

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  • ; palladium; silicon; Introduction The development of transition metal-catalyzed cross-coupling technologies over the last four decades revolutionized the synthetic chemistry. Indeed, the importance of Pd-catalyzed coupling was recognized with the 2010 Nobel Prize awarded to Heck, Negishi and Suzuki [1][2
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Published 11 Oct 2017
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