Practical synthesis of aryl-2-methyl-3-butyn-2-ols from aryl bromides via conventional and decarboxylative copper-free Sonogashira coupling reactions

• Andrea Caporale,
• Stefano Tartaggia,
• Andrea Castellin and
• Ottorino De Lucchi

Beilstein J. Org. Chem. 2014, 10, 384–393, doi:10.3762/bjoc.10.36

• terminal acetylenes is the most straightforward method for the preparation of substituted alkynes [1][2][3][4][5][6], which are extensively used as building blocks in a great number of applications including the synthesis of pharmaceuticals [7][8][9], natural products and organic functional materials [10

Triphenylene discotic liquid crystal trimers synthesized by Co₂(CO)₈-catalyzed terminal alkyne [2 + 2 + 2] cycloaddition

• Bin Han,
• Ping Hu,
• Bi-Qin Wang,
• Carl Redshaw and
• Ke-Qing Zhao

Beilstein J. Org. Chem. 2013, 9, 2852–2861, doi:10.3762/bjoc.9.321

• DLC oligomers can be divided into conventional organic reactions and transition metal-catalyzed synthetic methods. The use of transition metal-mediated reactions for constructing new organic functional materials is more efficient and therefore attractive. Our group has embarked upon a program to use

Ambient gold-catalyzed O-vinylation of cyclic 1,3-diketone: A vinyl ether synthesis

• Yumeng Xi,
• Boliang Dong and
• Xiaodong Shi

Beilstein J. Org. Chem. 2013, 9, 2537–2543, doi:10.3762/bjoc.9.288

• products are highly functional materials, which can be easily extended to complex molecules through simple transformations. 1,3-Cyclohexanedione and phenylacetylene were used as the model substrates for the evaluation of various gold catalysts. As shown in Table 1, the use of Ph3PAuCl/AgOTf (5%) gave an

Oxidative 3,3,3-trifluoropropylation of arylaldehydes

• Akari Ikeda,
• Masaaki Omote,
• Shiho Nomura,
• Miyuu Tanaka,
• Atsushi Tarui,
• Kazuyuki Sato and
• Akira Ando

Beilstein J. Org. Chem. 2013, 9, 2417–2421, doi:10.3762/bjoc.9.279

• , agricultural chemicals, and functional materials because trifluoromethylation of such chemicals often significantly improves their performance [1][2][3][4][5][6]. To date, the trifluoromethylation of carbonyl compounds [7][8][9][10] and aryl halides [11][12][13] has been extensively explored. On the other hand

Self-assembly of 2,3-dihydroxycholestane steroids into supramolecular organogels as a soft template for the in-situ generation of silicate nanomaterials

• Valeria C. Edelsztein,
• Andrea S. Mac Cormack,
• Matías Ciarlantini and
• Pablo H. Di Chenna

Beilstein J. Org. Chem. 2013, 9, 1826–1836, doi:10.3762/bjoc.9.213

• of their unique properties and numerous potential applications in fields such as the stabilization of organic photochromatic materials, the templated synthesis of nanostructured and functional materials, the controlled release drugs systems, the capture of spilled pollutants in the environment

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

• compounds in a wide range of applications in organic chemistry, as reagents, intermediates, ligands, bioactive agents, and functional materials [1][2][3][4]. The synthesis of organophosphorus compounds has therefore been extensively investigated (Scheme 1). Classical methods to form a C–P bond include ionic

Ring-opening reaction of 2,5-dioctyldithieno[2,3-b:3',2'-d]thiophene in the presence of aryllithium reagents

• Hao Zhong,
• Jianwu Shi,
• Jianxun Kang,
• Shaomin Wang,
• Xinming Liu and
• Hua Wang

Beilstein J. Org. Chem. 2013, 9, 767–774, doi:10.3762/bjoc.9.87

• Hao Zhong Jianwu Shi Jianxun Kang Shaomin Wang Xinming Liu Hua Wang Key Lab for Special Functional Materials of Ministry of Education, Henan University, Kaifeng, 475004, China Department of Chemistry, Zhengzhou University, Zhengzhou, 450001, China 10.3762/bjoc.9.87 Abstract In this paper, the

• . To construct DTT functional materials, deprotonation of DTT with organolithium reagents seems to be one of the most important approaches. However, the ring-opening reaction of DTT leading to the cleavage of the center ring can be observed in the presence of n-BuLi. In our previous work, we reported

Spin state switching in iron coordination compounds

• Philipp Gütlich,
• Ana B. Gaspar and
• Yann Garcia

Beilstein J. Org. Chem. 2013, 9, 342–391, doi:10.3762/bjoc.9.39

Features of the behavior of 4-amino-5-carboxamido-1,2,3-triazole in multicomponent heterocyclizations with carbonyl compounds

• Eugene S. Gladkov,
• Katerina A. Gura,
• Svetlana M. Sirko,
• Sergey M. Desenko,
• Ulrich Groth and
• Valentin A. Chebanov

Beilstein J. Org. Chem. 2012, 8, 2100–2105, doi:10.3762/bjoc.8.236

• Eugene S. Gladkov Katerina A. Gura Svetlana M. Sirko Sergey M. Desenko Ulrich Groth Valentin A. Chebanov Division of Chemistry of Functional Materials, State Scientific Institution “Institute for Single Crystals” of National Academy of Sciences of Ukraine, Lenin Ave. 60, 61158 Kharkiv, Ukraine

Design and synthesis of quasi-diastereomeric molecules with unchanging central, regenerating axial and switchable helical chirality via cleavage and formation of Ni(II)–O and Ni(II)–N coordination bonds

• Vadim A. Soloshonok,
• José Luis Aceña,
• Hisanori Ueki and
• Jianlin Han

Beilstein J. Org. Chem. 2012, 8, 1920–1928, doi:10.3762/bjoc.8.223

• *) and (Ra*,Ph*,Rc*) occurs by intramolecular trans-coordination of Ni–NH and Ni–O bonds providing a basis for a chiral switch model. Keywords: axial chirality; central chirality; chiral switches; coordination bonds; functional materials; helical chirality; modular structural design; molecular devices

Synthetic approaches to multifunctional indenes

• Neus Mesquida,
• Sara López-Pérez,
• Immaculada Dinarès and
• Ermitas Alcalde

Beilstein J. Org. Chem. 2011, 7, 1739–1744, doi:10.3762/bjoc.7.204

• ; amides; indanones; indenes; organometallic reagents; Introduction Compounds with an indene core are of great interest as precursors of metallocene complexes for catalytic polymerization processes, as well as being present in N-heterocyclic carbene ligands and functional materials [1][2][3][4][5][6][7][8

• elaboration of a variety of indene-based molecular modules with applications in fields as diverse as bioactive compounds, ligand precursors for metallocene catalyst systems, and functional materials. Key NMR responses for compounds 17, 19 and 23: 1D NOESY experiments. Retrosynthetic pathways to 3,5

Expanding the gelation properties of valine-based 3,5-diaminobenzoate organogelators with N-alkylurea functionalities

• Hak-Fun Chow and
• Chin-Ho Cheng

Beilstein J. Org. Chem. 2010, 6, 1015–1021, doi:10.3762/bjoc.6.114

• Hak-Fun Chow Chin-Ho Cheng Department of Chemistry, The Chinese University of Hong Kong, Shatin, NT, Hong Kong SAR The Center of Novel Functional Molecules, The Chinese University of Hong Kong, Shatin, NT, Hong Kong SAR Institute of Molecular Functional Materials, Areas of Excellence Scheme

Towards racemizable chiral organogelators

• Jian Bin Lin,
• Debarshi Dasgupta,
• Seda Cantekin and
• Albertus P. H. J. Schenning

Beilstein J. Org. Chem. 2010, 6, 960–965, doi:10.3762/bjoc.6.107

• advanced materials and constrained media for chiral synthesis and separation [3][4][5]. The development of systems where the chiral supramolecular assembly responds to specific triggers, should facilitate the design of smart functional materials in which subtle molecular-scale changes have an impact on the

Synthesis and crystal structures of multifunctional tosylates as basis for star-shaped poly(2-ethyl-2-oxazoline)s

• Richard Hoogenboom,
• Martin W. M. Fijten,
• Guido Kickelbick and
• Ulrich S. Schubert

Beilstein J. Org. Chem. 2010, 6, 773–783, doi:10.3762/bjoc.6.96

• of well-defined polymer architectures is of major importance for the development of complex functional materials. In this contribution, we discuss the synthesis of a range of multifunctional star-shaped tosylates as potential initiators for the living cationic ring-opening polymerization (CROP) of 2

Shelf-stable electrophilic trifluoromethylating reagents: A brief historical perspective

• Norio Shibata,
• Andrej Matsnev and
• Dominique Cahard

Beilstein J. Org. Chem. 2010, 6, No. 65, doi:10.3762/bjoc.6.65

• industry, due to the significant unique features that trifluoromethylated compounds have in pharmaceuticals, agricultural chemicals, and functional materials. Several effective reagents have been developed by the groups of Yagupolskii, Umemoto, Shreeve, Adachi, Magnier, Togni and Shibata. Due to the high

Preparation of pyridine-3,4-diols, their crystal packing and their use as precursors for palladium-catalyzed cross-coupling reactions

• Tilman Lechel,
• Irene Brüdgam and
• Hans-Ulrich Reissig

Beilstein J. Org. Chem. 2010, 6, No. 42, doi:10.3762/bjoc.6.42

• numerous naturally occurring compounds and are also frequently used in functional materials [1][2][3][4]. Pyridindiol derivatives are of particular interest as building blocks for the construction of dendritic nanostructures in supramolecular chemistry [5], whereas N-protected pyridine-3,4-diols find

The C–F bond as a conformational tool in organic and biological chemistry

• Luke Hunter

Beilstein J. Org. Chem. 2010, 6, No. 38, doi:10.3762/bjoc.6.38

• dipole moment caused by the orientation of all four fluorine atoms on the same face of the molecule. Overall, this work illustrates that a basic knowledge of the conformational preferences of multi-vicinal fluoroalkanes can have a valuable bearing on the design of functional materials. Peptides and

The efficient synthesis of dibenzo[d,d′]benzo[1,2-b:4,3-b′]dithiophene and cyclopenta[1,2-b:4,3-b′]bis(benzo[d]thiophen)-6-one

• Zhihua Wang,
• Sheng Zhu,
• Jianwu Shi and
• Hua Wang

Beilstein J. Org. Chem. 2009, 5, No. 55, doi:10.3762/bjoc.5.55

• Zhihua Wang Sheng Zhu Jianwu Shi Hua Wang Key Lab for Special Functional Materials of Ministry of Education, Henan University, Kaifeng 475004, China College of Chemistry and Chemical Engineering, Henan University, Kaifeng 475004, China 10.3762/bjoc.5.55 Abstract With 3,3′-bi[benzo[b]thiophenyl

• facilitate the synthetic approaches to various organic functional materials, by using 1 and 2 as building blocks, and/or versatile intermediates. The measurement of the hole/electron mobilities of compounds 1 and 2 is in progress. Experimental Synthesis of [3,3′]bi[benzo[b]thiophenyl]-2,2′-dicarbaldehyde (4

Functional properties of metallomesogens modulated by molecular and supramolecular exotic arrangements

• Alessandra Crispini,
• Mauro Ghedini and
• Daniela Pucci

Beilstein J. Org. Chem. 2009, 5, No. 54, doi:10.3762/bjoc.5.54

• single molecule to supramolecular network, confirming that metal coordination provides a helpful tool for obtaining multifunctional soft materials. Keywords: coordination complexes; functionality; liquid crystals; metallomesogens; Introduction Recent interest in designing novel soft and functional

• materials with more and more challenging requirements such as improved charge transport, luminescence, chirality and biological functions for high-tech applications has been directed towards the use of new mesomorphic systems [1][2][3][4][5][6][7][8][9][10][11][12][13][14]. Design principles based only on

Novel banana-discotic hybrid architectures

• Hari Krishna Bisoyi,
• H. T. Srinivasa and
• Sandeep Kumar

Beilstein J. Org. Chem. 2009, 5, No. 52, doi:10.3762/bjoc.5.52

• , smectic and columnar phases. On the other hand, the unique geometry of the columnar mesophase formed by discotic liquid crystals is of great importance not only as models for the study of one-dimensional charge and energy migration in organized systems but also as functional materials for device

From discovery to production: Scale- out of continuous flow meso reactors

• Peter Styring and
• Ana I. R. Parracho

Beilstein J. Org. Chem. 2009, 5, No. 29, doi:10.3762/bjoc.5.29

• ; Introduction Cross-coupling reactions are an essential tool in organic synthesis, from pharmaceuticals through to functional materials. In the majority of cases on the laboratory scale, coupling reactions are performed in stirred batch reactors such as round-bottom flasks using homogeneous catalysts and often

Synthesis of methylenebisamides using CC- or DCMT- activated DMSO

• Qiang Wang,
• Lili Sun,
• Yu Jiang and
• Chunbao Li

Beilstein J. Org. Chem. 2008, 4, No. 51, doi:10.3762/bjoc.4.51

• Qiang Wang Lili Sun Yu Jiang Chunbao Li Department of Chemistry, College of Science, Tianjin University, Tianjin 300072, China State Key Laboratory Base of Novel Functional Materials and Preparation Science at Ningbo, Faculty of Materials Science and Chemical Engineering, Ningbo University, Ningbo