Ligand effects, solvent cooperation, and large kinetic solvent deuterium isotope effects in gold(I)-catalyzed intramolecular alkene hydroamination

• Ruichen Lan,
• Brock Yager,
• Yoonsun Jee,
• Cynthia S. Day and
• Amanda C. Jones

Beilstein J. Org. Chem. 2024, 20, 479–496, doi:10.3762/bjoc.20.43

• hydroamination (1b) a KIE of 2.4 is estimated based on their statement of percent conversions in MeOH (61%) compared to MeOH-d4 (25%) after 20 hours at 50 °C [7]. Large isotope effects (>7) have been seen in a number of organometallic reactions [75] and tunneling need not be invoked if proton transfer involves

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

• relatively small, but experienced significant growth in recent times. In the early 1990s, the first examples of mechanochemical organometallic reactions were discovered, included the synthesis of various indenyl, cyclopentadienyl and metallocarborane complexes [174]. In Scheme 45, few examples of

Enabling technologies and green processes in cyclodextrin chemistry

• Giancarlo Cravotto,
• Marina Caporaso,
• Laszlo Jicsinszky and
• Katia Martina

Beilstein J. Org. Chem. 2016, 12, 278–294, doi:10.3762/bjoc.12.30

• . The catalytic hydrogenation of 6I-azido-6I-deoxy-β-CD using Pd/C was achieved under US irradiation in MeOH/H2O in 20 min (20.4 kHz, 80 W, yield: 88%); hydrogen was supplied at 1 bar pressure [15]. Sonochemical metals depassivation in organometallic reactions is well established [17]. A typical example

Synthesis and characterization of a hyper-branched water-soluble β-cyclodextrin polymer

• Francesco Trotta,
• Fabrizio Caldera,
• Roberta Cavalli,
• Andrea Mele,
• Carlo Punta,
• Lucio Melone,
• Franca Castiglione,
• Barbara Rossi,
• Monica Ferro,
• Vincenza Crupi,
• Domenico Majolino,
• Valentina Venuti and
• Dominique Scalarone

Beilstein J. Org. Chem. 2014, 10, 2586–2593, doi:10.3762/bjoc.10.271

• organometallic reactions [1] to emulsion polymerization [2][3][4]. By reacting CDs with suitable crosslinking agents, nanostructured hyper-cross-linked materials, known as nanosponges, can be obtained [5][6][7]. Currently there is a growing interest in the synthesis of soluble β-CD-based polymers, which is a

Aerobic radical multifunctionalization of alkenes using tert-butyl nitrite and water

• Daisuke Hirose and
• Tsuyoshi Taniguchi

Beilstein J. Org. Chem. 2013, 9, 1713–1717, doi:10.3762/bjoc.9.196

• useful methods because they can provide a shortcut to desired products. Various methods used widely, such as organometallic reactions, cycloaddition reactions and multicomponent reactions, are utilized for multifunctionalization [1][2][3][4][5]. If direct functionalization reactions of inactivated bonds

Some aspects of radical chemistry in the assembly of complex molecular architectures

• Béatrice Quiclet-Sire and
• Samir Z. Zard

Beilstein J. Org. Chem. 2013, 9, 557–576, doi:10.3762/bjoc.9.61

• past three decades [2][3][4][5]. Radicals offer many of the properties desired by synthetic organic chemists, as compared to ionic or organometallic reactions: generally mild and neutral experimental conditions; lower sensitivity to steric hindrance; lower susceptibility to the solvent effects; lesser

• tendency for rearrangements and β-elimination; and a selectivity that is often complementary to that of ionic or organometallic reactions, making some protection steps superfluous. Radicals are ambiphilic species that can react with both electron-poor and electron-rich substrates, but the rates can differ

Impact of cyclodextrins on the behavior of amphiphilic ligands in aqueous organometallic catalysis

• Hervé Bricout,
• Estelle Léonard,
• Christophe Len,
• David Landy,
• Frédéric Hapiot and
• Eric Monflier

Beilstein J. Org. Chem. 2012, 8, 1479–1484, doi:10.3762/bjoc.8.167

• , we are currently widening the scope of the CD/amphiphilic phosphane interaction in other aqueous-phase organometallic reactions. Water-soluble phosphanes 1–4. 2D T-ROESY NMR spectrum of a stoichiometric mixture of β-CD and 4 (3 mM each) in D2O at 20 °C. Effect of increasing concentrations of β-CD

Synthesis of diverse indole libraries on polystyrene resin – Scope and limitations of an organometallic reaction on solid supports

• Kerstin Knepper,
• Sylvia Vanderheiden and
• Stefan Bräse

Beilstein J. Org. Chem. 2012, 8, 1191–1199, doi:10.3762/bjoc.8.132

• ]. Organometallic reactions on solid supports are always particularly challenging [25]. In the past, indoles were synthesized by using, for example, Fischer indole synthesis [26][27][28][29][30], Bartoli indole synthesis, Nenitzescu synthesis [31], Wittig indole synthesis [32], Madelung indole synthesis [33

• as alkaloids or peptides, and various synthetic compounds [1][2]. Moreover, a large number of indole-containing compounds show potential as therapeutic agents. A large number of synthetic approaches have been published over the past hundred years. Recently, versatile and modular organometallic

• reactions have been used to create the indole core. Among these, the Bartoli reaction is a straightforward route for the generation of the indole moiety starting from nitroarenes. Some limitations of this useful reaction have been reported, e.g., only ortho-substituted nitroarenes gave good yields of the

Sonogashira–Hagihara reactions of halogenated glycals

• Dennis C. Koester and
• Daniel B. Werz

Beilstein J. Org. Chem. 2012, 8, 675–682, doi:10.3762/bjoc.8.75

• monosaccharide, this approach is unique due to its use of fully functionalized sugars, thus avoiding further refunctionalization steps to obtain the native C-glycoside. Results and Discussion Despite the numerous organometallic reactions performed with substituted glycals, to the best of our knowledge there has

Branching out at C-2 of septanosides. Synthesis of 2-deoxy-2-C-alkyl/aryl septanosides from a bromo-oxepine

• Supriya Dey and
• Narayanaswamy Jayaraman

Beilstein J. Org. Chem. 2012, 8, 522–527, doi:10.3762/bjoc.8.59

• common bromo-oxepine intermediate, involving C–C bond forming organometallic reactions. Unsaturated, seven-membered septanoside vinyl bromides or bromo-oxepines, obtained through a ring expansion methodology of the cyclopropane derivatives of oxyglycals, displayed a good reactivity towards several

• bond formation with alkyl and aryl substituents. Keywords: C–C bond formations; 2-deoxy sugars; organometallic reactions; septanosides; unsaturated sugars; Introduction Septanoses and septanosides are unnatural, seven-membered cyclic sugars [1]. Methods of preparation and the exploration of the

• envisaged that III would form as a synthon to implement C–C bond forming reactions. Vinyl halide 2 was synthesized through a ring-expansion reaction of cyclopropanated adduct 1 (Scheme 1), as reported previously [21]. The reactivity at C-2 of 2 was examined by the chosen organometallic reactions, namely

Synthesis of 5-(2-methoxy-1-naphthyl)- and 5-[2-(methoxymethyl)-1-naphthyl]-11H-benzo[b]fluorene as 2,2'-disubstituted 1,1'-binaphthyls via benzannulated enyne–allenes

• Yu-Hsuan Wang,
• Joshua F. Bailey,
• Jeffrey L. Petersen and
• Kung K. Wang

Beilstein J. Org. Chem. 2011, 7, 496–502, doi:10.3762/bjoc.7.58

• groups at various positions of the 1,1'-binaphthyl system. Transformation of the methoxy group in 20b to a hydroxy group provides a handle for resolution with optically active reagents. Experimental General information All organometallic reactions were conducted in oven-dried (120 °C) glassware under a

About the activity and selectivity of less well-known metathesis catalysts during ADMET polymerizations

• Hatice Mutlu,
• Lucas Montero de Espinosa,
• Oĝuz Türünç and
• Michael A. R. Meier

Beilstein J. Org. Chem. 2010, 6, 1149–1158, doi:10.3762/bjoc.6.131

• ; metathesis; olefin isomerization; renewable raw materials; ruthenium–indenylidene catalysts; Introduction Among the large number of organic and organometallic reactions allowing the formation of carbon–carbon bonds, olefin metathesis has found its place in organic synthesis as well as polymer science as a

Reduction of arenediazonium salts by tetrakis(dimethylamino)ethylene (TDAE): Efficient formation of products derived from aryl radicals

• Mohan Mahesh,
• John A. Murphy,
• Franck LeStrat and
• Hans Peter Wessel

Beilstein J. Org. Chem. 2009, 5, No. 1, doi:10.3762/bjoc.5.1

• donor in specific organometallic reactions, such as the chromium-mediated allylation of aldehydes and ketones [54][55] and the palladium-catalyzed reductive homo-coupling of aryl halides to afford the corresponding biaryls [56][57][58][59] illustrate further versatility of the reagent. The fact that

Trifluoromethyl ethers – synthesis and properties of an unusual substituent

• Frédéric R. Leroux,
• Baptiste Manteau,
• Jean-Pierre Vors and
• Sergiy Pazenok

Beilstein J. Org. Chem. 2008, 4, No. 13, doi:10.3762/bjoc.4.13

• ] and acylation [52][64]. Attack at the meta position has so far been observed only with the isopropylation and ethylation of (trifluoromethoxy)benzene (to the extent of 9 and 31%, respectively) [52]. Organometallic Reactions Some very versatile methodology functionalizing trifluoromethoxy substituted