Recent advances in transition metal-catalyzed Csp²-monofluoro-, difluoro-, perfluoromethylation and trifluoromethylthiolation

• Grégory Landelle,
• Armen Panossian,
• Sergiy Pazenok,
• Jean-Pierre Vors and
• Frédéric R. Leroux

Beilstein J. Org. Chem. 2013, 9, 2476–2536, doi:10.3762/bjoc.9.287

An investigation of the observed, but counter-intuitive, stereoselectivity noted during chiral amine synthesis via N-chiral-ketimines

• Thomas C. Nugent,
• Richard Vaughan Williams,
• Andrei Dragan,
• Alejandro Alvarado Méndez and
• Andrei V. Iosub

Beilstein J. Org. Chem. 2013, 9, 2103–2112, doi:10.3762/bjoc.9.247

• transition metal catalysis [5][6][7][8] and as resolving agents [9]. Despite their high demand, the ability to produce structurally diverse chiral amines has not kept pace. Spurred by this shortcoming, innovative and improved chemical methods have been developed over the last fifteen years. Among them

Post-Ugi gold-catalyzed diastereoselective domino cyclization for the synthesis of diversely substituted spiroindolines

• Amit Kumar,
• Dipak D. Vachhani,
• Sachin G. Modha,
• Sunil K. Sharma,
• Virinder S. Parmar and
• Erik V. Van der Eycken

Beilstein J. Org. Chem. 2013, 9, 2097–2102, doi:10.3762/bjoc.9.246

• materials. Based on this work and our continuous interest in transition metal catalysis [45][46][47][48][49][50][51][52][53][54], multicomponent reactions [55][56][57] and the chemistry of the indole core [58][59][60], we herein report a post-Ugi gold-catalyzed intramolecular domino cyclization sequence for

Homolytic substitution at phosphorus for C–P bond formation in organic synthesis

• Hideki Yorimitsu

Beilstein J. Org. Chem. 2013, 9, 1269–1277, doi:10.3762/bjoc.9.143

• reactions such as nucleophilic substitution of P–X compounds with organometallic reagents, nucleophilic substitution of alkyl halides with phosphorus nucleophiles, and nucleophilic addition to polar unsaturated bonds. Recent advances in transition-metal catalysis have realized catalytic cross-coupling

Efficient Cu-catalyzed base-free C–S coupling under conventional and microwave heating. A simple access to S-heterocycles and sulfides

• Silvia M. Soria-Castro and
• Alicia B. Peñéñory

Beilstein J. Org. Chem. 2013, 9, 467–475, doi:10.3762/bjoc.9.50

• compounds. The formation of C–S bonds can also be accomplished in good to excellent yields by transition-metal catalysis [10][11], mainly using palladium [12], copper [13][14][15][16], nickel [17][18] and iron [19][20] salts. Aryl coupling reactions employing different palladium species as catalysts

Recent advances in direct C–H arylation: Methodology, selectivity and mechanism in oxazole series

• Cécile Verrier,
• Pierrik Lassalas,
• Laure Théveau,
• Guy Quéguiner,
• François Trécourt,
• Francis Marsais and
• Christophe Hoarau

Beilstein J. Org. Chem. 2011, 7, 1584–1601, doi:10.3762/bjoc.7.187

• in this article. Methodologies, selectivity, mechanism and future aspects are presented. Keywords: ate complex; catalytic direct arylation; mechanism; oxazole; selectivity; transition-metal catalysis; Introduction Deprotonative metalation of aromatics is widely used as a powerful method for

One-pot four-component synthesis of pyrimidyl and pyrazolyl substituted azulenes by glyoxylation–decarbonylative alkynylation–cyclocondensation sequences

• Charlotte F. Gers,
• Julia Rosellen,
• Eugen Merkul and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2011, 7, 1173–1181, doi:10.3762/bjoc.7.136

• traditional multistep syntheses. Thus, they can be considered to be economically and ecologically efficient [9][10]. In particular, multicomponent syntheses of heterocycles initiated by transition metal catalysis received increasing attention in the past decade [11]. As a one-pot synthetic methodology, this

• novel concept combines the unique reactivity patterns of transition metal catalysis with fundamental organic reactivity, in a sequential or consecutive fashion. Over the years, we have contributed to this concept through Pd/Cu-catalyzed accesses to enones and ynones and the in situ transformation of

Multicomponent reactions

• Thomas J. J. Müller

Beilstein J. Org. Chem. 2011, 7, 960–961, doi:10.3762/bjoc.7.107

• lead structures of active agents, catalysts and even novel molecule-based materials. This Thematic Series on multicomponent reactions represents a snapshot of a highly dynamic field and spans a broad range, from recent advances in isonitrile-based MCR to transition metal catalysis in MCR; from peptidic

Highly efficient gold(I)-catalyzed Overman rearrangement in water

• Dong Xing and
• Dan Yang

Beilstein J. Org. Chem. 2011, 7, 781–785, doi:10.3762/bjoc.7.88

• allylic trichloroacetimidates to allylic trichloroacetamides (Overman rearrangement) is a powerful and attractive strategy for the synthesis of allylic amines from readily available allylic alcohols [1][2]. This transformation can be conducted thermally at high temperatures or by transition metal

• catalysis under very mild conditions [3][4][5][6][7]. Asymmetric induction has been achieved with certain types of transition metal catalysts (e.g., palladium complexes) in combination with chiral ancillary ligands [8][9][10][11][12][13]. However, although a large number of late transition metal catalysts

Continuous flow hydrogenation using polysilane-supported palladium/alumina hybrid catalysts

• Hidekazu Oyamada,
• Takeshi Naito and
• Shū Kobayashi

Beilstein J. Org. Chem. 2011, 7, 735–739, doi:10.3762/bjoc.7.83

• and substantially increase production. We also recently reported novel transition metal catalysis involving the immobilization of Pd or Pt onto polysilane supports by the microencapsulation method [12]. The Pd catalyst (Pd/PSi) had high activity with no or very little leaching of Pd, and it could be

Suzuki–Miyaura cross-coupling reaction of 1-aryltriazenes with arylboronic acids catalyzed by a recyclable polymer-supported N-heterocyclic carbene–palladium complex catalyst

• Guangming Nan,
• Fang Ren and
• Meiming Luo

Beilstein J. Org. Chem. 2010, 6, No. 70, doi:10.3762/bjoc.6.70

• , arylsulfonyl chlorides and arenediazonium salts with arylboronic acids that gave biaryls in good to excellent yields [28][31][32]. As part of our ongoing investigations aimed at the development of transition metal catalysis, we report here that the Suzuki–Miyaura cross-couplings of 1-aryltriazenes with

A thermally-induced, tandem [3,3]-sigmatropic rearrangement/[2 + 2] cycloaddition approach to carbocyclic spirooxindoles

• Kay M. Brummond and
• Joshua M. Osbourn

Beilstein J. Org. Chem. 2010, 6, No. 33, doi:10.3762/bjoc.6.33

• rearrangement of the propargyl acetate 9a using transition metal catalysis (AuCl3 10 mol %, toluene, 1 h, rt) led to hydrolysis of the allenyl acetate functionality. This densely functionalized alkylidene cyclobutene 10a is postulated to arise via the [2 + 2] cycloaddition reaction between the alkyne and the

A review of new developments in the Friedel–Crafts alkylation – From green chemistry to asymmetric catalysis

• Magnus Rueping and
• Boris J. Nachtsheim

Beilstein J. Org. Chem. 2010, 6, No. 6, doi:10.3762/bjoc.6.6

• simultaneously, an acid-catalyzed ortho-arylation of aniline employing the strong Brønsted acid PhNH3B(C6F5)4•Et2O was developed by Bergman et al. indicating the close relationship between strong Brønsted acid- and transition-metal catalysis [70]. A double ortho-hydroarylation of anilines with styrenes was

• optical active ligands for enantioselective transition-metal catalysis (Scheme 22) [71]. To the best of our knowledge, efficient ortho-benzylations of anilines with benzyl alcohols as alkylating reagents have yet to be described [15]. Catalytic Friedel–Crafts allylations Allylated arenes represent

Can we measure catalyst efficiency in asymmetric chemical reactions? A theoretical approach

• Shaimaa El-Fayyoumy,
• Matthew H. Todd and
• Christopher J. Richards

Beilstein J. Org. Chem. 2009, 5, No. 67, doi:10.3762/bjoc.5.67

• chemistry [1]. Enormous progress has been made in recent years, most notably in homogenous transition metal catalysis, organocatalysis and enzyme-catalysed reactions. It is therefore surprising that there is no generally accepted measure for the effectiveness of a catalytic reaction. That is to say when we

Expedient syntheses of the N-heterocyclic carbene precursor imidazolium salts IPr·HCl, IMes·HCl and IXy·HCl

• Lukas Hintermann

Beilstein J. Org. Chem. 2007, 3, No. 22, doi:10.1186/1860-5397-3-22

• involving a 1,5-dipolar electrocyclization is proposed. Background Imidazolylidene carbenes have been investigated as ligands in coordination chemistry, as powerful steering/controlling elements in transition-metal catalysis,[1][2] and more recently as metal-free catalysts for organic reactions[3][4]. Some

An exceptional P-H phosphonite: Biphenyl- 2,2'-bisfenchylchlorophosphite and derived ligands (BIFOPs) in enantioselective copper- catalyzed 1,4-additions

• T. Kop-Weiershausen,
• J. Lex,
• J.-M. Neudörfl and
• B. Goldfuss

Beilstein J. Org. Chem. 2005, 1, No. 6, doi:10.1186/1860-5397-1-6

• the phosphorus atoms in biphenyl-2,2'-bisfenchylphosphites (BIFOPs) founds the special suitability for BIFOP-H (3) as P-H phosphonite ligand in transition metal catalysis. This points to promising applications of 3 or analogue P-H ligands in enantioselective catalysis. X-ray crystal structure of BIFOP

Mixtures of monodentate P-ligands as a means to control the diastereoselectivity in Rh-catalyzed hydrogenation of chiral alkenes

• Manfred T. Reetz and
• Hongchao Guo

Beilstein J. Org. Chem. 2005, 1, No. 3, doi:10.1186/1860-5397-1-3

• new approach in the area of combinatorial asymmetric transition metal catalysis:[19][20] The use of mixtures of two chiral monodentate ligands La and Lb in metal catalysts of the type ML2, leading to two so-called homo-combinations and one hetero-combination which are in equilibrium with one another