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

Synthesis of benzannelated sultams by intramolecular Pd-catalyzed arylation of tertiary sulfonamides

  • Valentin A. Rassadin,
  • Mirko Scholz,
  • Anastasiia A. Klochkova,
  • Armin de Meijere and
  • Victor V. Sokolov

Beilstein J. Org. Chem. 2017, 13, 1932–1939, doi:10.3762/bjoc.13.187

Graphical Abstract
  • , sultams have been prepared employing Diels–Alder reactions, radical cyclizations, reductions of sulfonylimines, ring-closing metatheses, nucleophilic aromatic substitutions and Heck cyclizations [14][15][16]. Earlier on, our group has developed versatile syntheses of sultams based on the transformation of
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Published 12 Sep 2017

Mechanochemical synthesis of small organic molecules

  • Tapas Kumar Achar,
  • Anima Bose and
  • Prasenjit Mal

Beilstein J. Org. Chem. 2017, 13, 1907–1931, doi:10.3762/bjoc.13.186

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  • % of PCy3·HBF4 along with an excess K2CO3–MeOH led to biaryls within 99 min and with a yield up to 97% (Scheme 8) [57]. Heck reaction Frejd and co-workers reported the first mechanochemical Heck reaction [58]. Su and co-workers demonstrated that (E)-stilbene derivatives were synthesized by the coupling
  • . Easy purification procedures, towards quantitative conversion and minimum byproducts are additionally considered to be major significance to this method. Tullberg et al. investigated the Mizoroki–Heck reaction between iodobenzene and the methyl ester of N-Boc-protected aminoacylate under different
  • ]. Mechanochemical Suzuki reaction [56]. Mechanochemical Suzuki–Miyaura coupling by LAG [57]. Mechanochemical Heck reaction [59]. a) Sonogashira coupling under milling conditions. b) The representative example of a double Sonogashira reaction of p-iodoacetophenone with 1,4-bis-ethynyl benzene. Copper-catalyzed CDC
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Published 11 Sep 2017

Pd(OAc)2/Ph3P-catalyzed dimerization of isoprene and synthesis of monoterpenic heterocycles

  • Dominik Kellner,
  • Maximilian Weger,
  • Andrea Gini and
  • Olga García Mancheño

Beilstein J. Org. Chem. 2017, 13, 1807–1815, doi:10.3762/bjoc.13.175

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  • system PdBr2(dppe)/NaOPh/PhOH [31]. Furthermore, an interesting work by Heck and co-workers in 1976 already showed the possibility of generating the corresponding dimethyloctadienes of isoprene by a reductive dimerization in the presence of formic acid with the dimeric allylpalladium acetate catalyst and
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Published 29 Aug 2017

An efficient Pd–NHC catalyst system in situ generated from Na2PdCl4 and PEG-functionalized imidazolium salts for Mizoroki–Heck reactions in water

  • Nan Sun,
  • Meng Chen,
  • Liqun Jin,
  • Wei Zhao,
  • Baoxiang Hu,
  • Zhenlu Shen and
  • Xinquan Hu

Beilstein J. Org. Chem. 2017, 13, 1735–1744, doi:10.3762/bjoc.13.168

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  • materials via a simple method. Their corresponding water soluble Pd–NHC catalysts, in situ generated from the imidazolium salts L1–L3 and Na2PdCl4 in water, showed impressive catalytic activity for aqueous Mizoroki–Heck reactions. The kinetic study revealed that the Pd catalyst derived from the imidazolium
  • 10,000. Keywords: aqueous homogeneous catalysis; Mizoroki–Heck reaction; Na2PdCl4; PEG-functionalized imidazolium salts; Introduction Nowadays, both increasing environmental concerns and drastic commercial competition are the driving forces to develop more sustainable and economic processes for
  • contributed to Suzuki–Miyaura reactions and only a very few examples were reported for Mizoroki–Heck reactions [45][51][53][57]. Previous research by Rösch and other groups disclosed that introducing a hemilable donor group (such as N, O, S etc.) on the NHC rings was favorable for the palladium-catalyzed
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Published 21 Aug 2017

An effective Pd nanocatalyst in aqueous media: stilbene synthesis by Mizoroki–Heck coupling reaction under microwave irradiation

  • Carolina S. García,
  • Paula M. Uberman and
  • Sandra E. Martín

Beilstein J. Org. Chem. 2017, 13, 1717–1727, doi:10.3762/bjoc.13.166

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  • Mizoroki–Heck coupling reactions under microwave irradiation (MW) were carried out with a colloidal Pd nanocatalyst stabilized with poly(N-vinylpyrrolidone) (PVP). Many stilbenes and novel heterostilbenes were achieved in good to excellent yields starting from aryl bromides and different olefins. The
  • make this protocol a great option for stilbene syntheses by Mizoroki–Heck reaction. Keywords: aqueous reaction medium; MAOS; Mizoroki–Heck reaction; Pd nanoparticle; sustainable organic synthesis; Introduction Palladium-catalyzed reactions have emerged as an important tool for organic synthesis
  • both coupling partners. The Mizoroki–Heck reaction and related chemistry occupy a special place among the basic types of Pd-catalyzed reactions, particularly the vinylation of aryl/vinyl halides or triflates [7][8][9][10], explored not only in the inter- and intramolecular version [2][11][12][13], but
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Published 18 Aug 2017

Encaging palladium(0) in layered double hydroxide: A sustainable catalyst for solvent-free and ligand-free Heck reaction in a ball mill

  • Wei Shi,
  • Jingbo Yu,
  • Zhijiang Jiang,
  • Qiaoling Shao and
  • Weike Su

Beilstein J. Org. Chem. 2017, 13, 1661–1668, doi:10.3762/bjoc.13.160

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  • , Zhejiang, China 10.3762/bjoc.13.160 Abstract In this paper, the synthesis of a cheap, reusable and ligand-free Pd catalyst supported on MgAl layered double hydroxides (Pd/MgAl-LDHs) by co-precipitation and reduction methods is described. The catalyst was used in Heck reactions under high-speed ball
  • milling (HSBM) conditions at room temperature. The effects of milling-ball size, milling-ball filling degree, reaction time, rotation speed and grinding auxiliary category, which would influence the yields of mechanochemical Heck reactions, were investigated in detail. The characterization results of XRD
  • , ICP–MS and XPS suggest that Pd/MgAl-LDHs have excellent textural properties with zero-valence Pd on its layers. The reaction results indicate that the catalyst could be utilized in HSBM systems to afford a wide range of Heck coupling products in satisfactory yields. Furthermore, this catalyst could be
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Published 14 Aug 2017

Total syntheses of the archazolids: an emerging class of novel anticancer drugs

  • Stephan Scheeff and
  • Dirk Menche

Beilstein J. Org. Chem. 2017, 13, 1085–1098, doi:10.3762/bjoc.13.108

Graphical Abstract
  • suitable olefination strategy. Subsequently, for connecting the resulting fragment to the thiazole subunit 6 a Heck reaction was envisioned as part of studies advancing this type of Palladium-catalyzed coupling strategies in complex target synthesis [61][62][63][64][65][66]. Finally, a HWE-macrocyclization
  • synthesis, also on highly elaborate substrates. Considerable efforts were invested before the challenging Heck coupling with the thiazole fragment 6 could be effected with useful selectivities. Besides the desired E,E-diene 34 formation of other double bond isomers both in the southern and northern part of
  • unambiguously confirming the stereochemistry of this macrolide [59]. Menche’s total synthesis of archazolid B One the methodological incentives of the synthetic campaign of the Menche group directed towards the archazolids were the further development and application of the Heck reaction in complex target
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Published 07 Jun 2017

A strategic approach to [6,6]-bicyclic lactones: application towards the CD fragment of DHβE

  • Tue Heesgaard Jepsen,
  • Emil Glibstrup,
  • François Crestey,
  • Anders A. Jensen and
  • Jesper Langgaard Kristensen

Beilstein J. Org. Chem. 2017, 13, 988–994, doi:10.3762/bjoc.13.98

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  • effective synthetic protocol to access [6,6]-bicyclic lactone moieties through a regio- and stereoselective intramolecular Mizoroki–Heck cross-coupling reaction followed by a 6π-electrocyclization. This method enabled the first synthesis of the elusive CD fragment of the Erythrina alkaloid DHβE. Preliminary
  • pharmacological evaluations support the notion that the key pharmacophores of DHβE are located in the A and B rings. Keywords: DhβE; Mizoroki–Heck cross-coupling reaction; 6π-electrocyclization; [6,6]-bicyclic lactone; vinyl halide; Introduction The neuronal nicotinic acetylcholine receptors (nAChRs) have been
  • intramolecular Mizoroki–Heck cross-coupling reaction and a 6π-electrocyclization as key steps. Results and Discussion First strategy with Ts and Cbz protecting groups As depicted in Scheme 1, our first strategy featured a late stage installation of the lactonic D ring by a 6π-electrocyclization and formation of
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Published 22 May 2017

Synthesis of 1-indanones with a broad range of biological activity

  • Marika Turek,
  • Dorota Szczęsna,
  • Marek Koprowski and
  • Piotr Bałczewski

Beilstein J. Org. Chem. 2017, 13, 451–494, doi:10.3762/bjoc.13.48

Graphical Abstract
  • have applied a Heck-reduction–cyclization–alkylation (HRCA) methodology under mild and simple reaction conditions. First, diazonium salts 56 underwent the Heck reaction with methyl vinyl ketone (57) to give the cross-coupling products 58 followed by hydrogenation of the latter to give aromatic
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Published 09 Mar 2017

Synthesis and optical properties of new 5'-aryl-substituted 2,5-bis(3-decyl-2,2'-bithiophen-5-yl)-1,3,4-oxadiazoles

  • Anastasia S. Kostyuchenko,
  • Tatyana Yu. Zheleznova,
  • Anton J. Stasyuk,
  • Aleksandra Kurowska,
  • Wojciech Domagala,
  • Adam Pron and
  • Alexander S. Fisyuk

Beilstein J. Org. Chem. 2017, 13, 313–322, doi:10.3762/bjoc.13.34

Graphical Abstract
  • Discussion Synthetic toolbox It is well known that thiophenes containing acceptor groups such as CHO, CN or CO2Me at the C-2 position readily react with aryl halides in the presence of a Pd(II) catalyst through a Heck-type coupling [26]. We have synthesized the ethyl ester of 2,2'-bithiophene-5-carboxylic
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Published 17 Feb 2017

Highly bulky and stable geometry-constrained iminopyridines: Synthesis, structure and application in Pd-catalyzed Suzuki coupling of aryl chlorides

  • Yi Lai,
  • Zhijian Zong,
  • Yujie Tang,
  • Weimin Mo,
  • Nan Sun,
  • Baoxiang Hu,
  • Zhenlu Shen,
  • Liqun Jin,
  • Wen-hua Sun and
  • Xinquan Hu

Beilstein J. Org. Chem. 2017, 13, 213–221, doi:10.3762/bjoc.13.24

Graphical Abstract
  • showed a good catalytic efficiency for both Suzuki and Heck cross-coupling reactions. The favorable effect originated from the ring-fused framework being able to establish a strained environment for better stability. Efficient couplings were achieved with aryl bromides or iodides as substrates, however
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Published 03 Feb 2017

Efficient access to β-vinylporphyrin derivatives via palladium cross coupling of β-bromoporphyrins with N-tosylhydrazones

  • Vinicius R. Campos,
  • Ana T. P. C. Gomes,
  • Anna C. Cunha,
  • Maria da Graça P. M. S. Neves,
  • Vitor F. Ferreira and
  • José A. S. Cavaleiro

Beilstein J. Org. Chem. 2017, 13, 195–202, doi:10.3762/bjoc.13.22

Graphical Abstract
  • , affording in such way important intermediates for different synthetic strategies [4][17][18]. There are methods available allowing the insertion of alkenyl groups into porphyrin macrocycles (e.g., Heck reaction [4], metathesis [7][19][20][21], Wittig reaction [22][23]). However, palladium-catalyzed cross
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Published 30 Jan 2017

Poly(ethylene glycol)s as grinding additives in the mechanochemical preparation of highly functionalized 3,5-disubstituted hydantoins

  • Andrea Mascitti,
  • Massimiliano Lupacchini,
  • Ruben Guerra,
  • Ilya Taydakov,
  • Lucia Tonucci,
  • Nicola d’Alessandro,
  • Frederic Lamaty,
  • Jean Martinez and
  • Evelina Colacino

Beilstein J. Org. Chem. 2017, 13, 19–25, doi:10.3762/bjoc.13.3

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  • other alternative energy inputs is still scarce. Only three examples highlight their peculiar role for metal-catalysed processes in a ball mill (Mirozoki–Heck reaction) [6], by ultrasound (copper-catalysed cyanation reaction) [7], and for co-crystal formation in the polymer-assisted grinding process
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Published 04 Jan 2017

Iodination of carbohydrate-derived 1,2-oxazines to enantiopure 5-iodo-3,6-dihydro-2H-1,2-oxazines and subsequent palladium-catalyzed cross-coupling reactions

  • Michal Medvecký,
  • Igor Linder,
  • Luise Schefzig,
  • Hans-Ulrich Reissig and
  • Reinhold Zimmer

Beilstein J. Org. Chem. 2016, 12, 2898–2905, doi:10.3762/bjoc.12.289

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  • -forming reactions such as Sonogashira, Heck, or Suzuki coupling reactions as well as a cyanation reaction. These cross-coupling reactions led to a series of 5-alkynyl-, 5-alkenyl-, 5-aryl- and 5-cyano-substituted 1,2-oxazine derivatives being of considerable interest for further synthetic elaborations
  • -oxazine syn-11 in 41% yield. Next, we briefly studied 5-iodo-1,2-oxazine syn-4a as substrate in Heck reactions. The substrate was reacted with the alkyl acrylates 12a (R1 = Me) and 12b (R1 = t-Bu) under phosphine-free conditions [33][34] using 6 mol % of palladium(II) acetate, triethylamine as base and
  • lithium chloride [35] leading to the expected coupling products syn-13 and syn-14 in 39% and 82% yield, respectively (Scheme 5). In both cases, only the E-configured 2-substituted alkyl acrylates were isolated. The moderate yield in the Heck reaction with methyl acrylate 12a is very likely caused by the
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Published 29 Dec 2016

Direct arylation catalysis with chloro[8-(dimesitylboryl)quinoline-κN]copper(I)

  • Sem Raj Tamang and
  • James D. Hoefelmeyer

Beilstein J. Org. Chem. 2016, 12, 2757–2762, doi:10.3762/bjoc.12.272

Graphical Abstract
  • ]. Recently, we reported the Pd(II) complex catalyzed Heck-type C–C coupling [51]. The observation may implicate reductive elimination and oxidative addition can cycle repeatedly on the palladium center coordinated to 1. With this in mind, we sought to utilize the Cu(I) complex, chloro[8-(dimesitylboryl
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Published 15 Dec 2016

Rapid regio- and multi-coupling reactivity of 2,3-dibromobenzofurans with atom-economic triarylbismuths under palladium catalysis

  • Maddali L. N. Rao,
  • Jalindar B. Talode and
  • Venneti N. Murty

Beilstein J. Org. Chem. 2016, 12, 2065–2076, doi:10.3762/bjoc.12.195

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  • the synthesis of 2,3-dialkenylbenzofurans and functionalized dibenzofurans with domino “twofold Heck/6π-electrocyclization” of 2,3-di- and 2,3,5-tribromobenzofuran substrates [34]. In this regard, the cross-coupling studies of triarylbismuth reagents in regioselective studies with functionalized
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Published 22 Sep 2016

Scope and limitations of a DMF bio-alternative within Sonogashira cross-coupling and Cacchi-type annulation

  • Kirsty L. Wilson,
  • Alan R. Kennedy,
  • Jane Murray,
  • Ben Greatrex,
  • Craig Jamieson and
  • Allan J. B. Watson

Beilstein J. Org. Chem. 2016, 12, 2005–2011, doi:10.3762/bjoc.12.187

Graphical Abstract
  • ][35], Mizoroki–Heck [36][37], Sonogashira [38], Stille [39], Hiyama reactions [40], and hydroformylation reactions [41]. In the current study, we present the use of Cyrene as an alternative solvent (direct DMF replacement) for the Sonogashira reaction, as well as related Cacchi-type annulations [42
  • -used organic transformations. For example, the majority of many other standard cross-coupling processes employ inorganic or organic bases and heat (e.g., Suzuki–Miyaura, Heck). Accordingly, Cyrene may be projected to be incompatible with standard conditions for these reactions and its use would
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Published 08 Sep 2016

Stereoselective synthesis of tricyclic compounds by intramolecular palladium-catalyzed addition of aryl iodides to carbonyl groups

  • Jakub Saadi,
  • Christoph Bentz,
  • Kai Redies,
  • Dieter Lentz,
  • Reinhold Zimmer and
  • Hans-Ulrich Reissig

Beilstein J. Org. Chem. 2016, 12, 1236–1242, doi:10.3762/bjoc.12.118

Graphical Abstract
  • –R2 = (CH2)4] typical Heck reaction conditions employing styrene as olefin component not only led to the desired styrene derivative B but mainly to the cyclized product C. If the reaction was performed without the olefin it provided only the tertiary alcohol C in reasonable yield [5]. Similar C–C bond
  • structure (ORTEP, [14]) of compound 14a (thermal ellipsoids at 50% probability). Molecular structure (ORTEP, [14]) of compound 15a (thermal ellipsoids at 50% probability). Molecular structure (ORTEP [14]) of compound 15b (thermal ellipsoids at 50% probability). Planned Heck reaction of A to compound B and
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Published 16 Jun 2016

Cationic Pd(II)-catalyzed C–H activation/cross-coupling reactions at room temperature: synthetic and mechanistic studies

  • Takashi Nishikata,
  • Alexander R. Abela,
  • Shenlin Huang and
  • Bruce H. Lipshutz

Beilstein J. Org. Chem. 2016, 12, 1040–1064, doi:10.3762/bjoc.12.99

Graphical Abstract
  • generally resorted to elevated temperatures (80–160 °C) and anhydrous conditions, and in many cases high pressures of CO or O2 are also required in order to carry out these Heck-like coupling reactions [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20][21][22][193][194][195][196][197
  • results in the formation of a monocationic arylpalladium(II) palladacycle, likely via a Wheland-like intermediate (Scheme 23) [233][234][235][236][237]. The product-forming portion of the cycle may proceed in a manner resembling a traditional Heck cross-coupling. In this case, addition of the palladacycle
  • to an acrylate followed by β-hydride elimination yields the corresponding product 5. As previously demonstrated in palladium-catalyzed Mizoroki–Heck reactions [238][239][240], insertion of a alkenyl double bond into C–Pd+ present within the cationic palladacyle is facile, owing to the high Lewis
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Published 20 May 2016

Enantioselective carbenoid insertion into C(sp3)–H bonds

  • J. V. Santiago and
  • A. H. L. Machado

Beilstein J. Org. Chem. 2016, 12, 882–902, doi:10.3762/bjoc.12.87

Graphical Abstract
  • activation; chiral catalysis; diazo compounds; total synthesis; Introduction One of the major challenges met in organic synthesis is the formation of carbon–carbon bonds, in particular in a stereoselective way. Nucleophilic substitution reactions, radical reactions, cross-coupling reactions and the Heck
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Published 04 May 2016

A modular approach to neutral P,N-ligands: synthesis and coordination chemistry

  • Vladislav Vasilenko,
  • Torsten Roth,
  • Clemens K. Blasius,
  • Sebastian N. Intorp,
  • Hubert Wadepohl and
  • Lutz H. Gade

Beilstein J. Org. Chem. 2016, 12, 846–853, doi:10.3762/bjoc.12.83

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  • hydrogenations [1][2] and allylic substitutions [3][4] to Heck reactions [5] and conjugate additions to enones [6]. Their popularity arises from the inherent electronic disparity of the phosphorus and the nitrogen donor groups, rendering one binding site a soft π-acceptor featuring a pronounced trans effect and
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Published 29 Apr 2016

A selective and mild glycosylation method of natural phenolic alcohols

  • Mária Mastihubová and
  • Monika Poláková

Beilstein J. Org. Chem. 2016, 12, 524–530, doi:10.3762/bjoc.12.51

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  • ]. Isoconiferin (3) has been prepared mainly by the trichloroacetimidate method [20][21] using 4-O-acetylated coniferyl alcohol as the acceptor. On the other hand, the Mizoroki–Heck reaction of 4-hydroxy-3-methoxyphenylboronic acid and peracetylated allyl β-D-glucoside has been used to synthesize 3 in 52% yield
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Published 15 Mar 2016

Study on the synthesis of the cyclopenta[f]indole core of raputindole A

  • Nils Marsch,
  • Mario Kock and
  • Thomas Lindel

Beilstein J. Org. Chem. 2016, 12, 334–342, doi:10.3762/bjoc.12.36

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  • , which was synthesized via Heck reaction with but-3-en-2-ol (5, 89%) in the presence of LiCl, inspired by a procedure by Camp and coworkers [36]. Propargyl bisindole 7 was obtained after conversion of 4 (2 equiv) to the magnesium acetylide (iPrMgCl in THF) and Grignard reaction with ketone 6. Due to the
  • ketone 26 proceeded in the highest yield of all our Meyer–Schuster rearrangements. With triflated α,β-unsaturated ketone 26 in hand, we attempted reductive Heck cyclizations to the raputindole core structure. For instance, we employed Pd(dba)2 (12 mol %), QPhos (24 mol %), and NEt3 (1.20 equiv) in DMF at
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Published 23 Feb 2016

Hydroquinone–pyrrole dyads with varied linkers

  • Hao Huang,
  • Christoffer Karlsson,
  • Maria Strømme,
  • Martin Sjödin and
  • Adolf Gogoll

Beilstein J. Org. Chem. 2016, 12, 89–96, doi:10.3762/bjoc.12.10

Graphical Abstract
  • derivatives and pyrrolylboronic acids should be possible. Ethylene linker: Synthesis of 3-(2,5-dimethoxystyryl)-1H-pyrrole (3c) Our initial approach of synthesizing vinyl linker dyad 3c was to use a Heck reaction, coupling 3-iodo-1-(triisopropylsilyl)-1H-pyrrole and dimethoxystyrene. A variation of reaction
  • , see Supporting Information File 2). According to a study by Liu et al. [19], the protecting group for 3-iodo pyrrole is essential in the Heck reaction involving pyrrole. Based on this suggestion, 3-iodo-1-tosyl-1H-pyrrole was also tested but did not result in any product. It is worth to mention that
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Published 18 Jan 2016

N-Methylphthalimide-substituted benzimidazolium salts and PEPPSI Pd–NHC complexes: synthesis, characterization and catalytic activity in carbon–carbon bond-forming reactions

  • Senem Akkoç,
  • Yetkin Gök,
  • İlhan Özer İlhan and
  • Veysel Kayser

Beilstein J. Org. Chem. 2016, 12, 81–88, doi:10.3762/bjoc.12.9

Graphical Abstract
  • complexes have been used in different coupling reactions such as Mizoroki–Heck cross-coupling [22][23], Suzuki–Miyaura cross-coupling [24][25], Sonogashira [26] and arylation reactions [27]. There are suitable precatalyst scaffolds, which were developed by Nolan [28], Organ [21] and Buchwald [29]. To find
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Published 15 Jan 2016
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