Pyridine C(sp²)–H bond functionalization under transition-metal and rare earth metal catalysis

• Haritha Sindhe,
• Malladi Mounika Reddy,
• Karthikeyan Rajkumar,
• Akshay Kamble,
• Amardeep Singh,
• Anand Kumar and
• Satyasheel Sharma

Beilstein J. Org. Chem. 2023, 19, 820–863, doi:10.3762/bjoc.19.62

• 210. In 2012, a hydroarylation of alkenes 211 and alkynes 212 with 2,2′-bipyridines 208 and 2,2′-biquinolines was reported by Chang and co-workers [112] in the presence of Rh(acac)3 as catalyst, IMes·HCl (3 mol %) as ligand and t-BuONa (30 mol %) in toluene for 2 h (Scheme 40). The authors

Synthesis of tetrasubstituted pyrazoles containing pyridinyl substituents

• Josef Jansa,
• Ramona Schmidt,
• Ashenafi Damtew Mamuye,
• Laura Castoldi,
• Alexander Roller,
• Vittorio Pace and
• Wolfgang Holzer

Beilstein J. Org. Chem. 2017, 13, 895–902, doi:10.3762/bjoc.13.90

• instance for 2,2’-bipyridines [43][44] and other comparable systems [45]. In Figure 1, complete NMR data for the tetrapyridinylpyrazole 9a are displayed, which permits to follow some of the trends regarding chemical shift considerations discussed above. Conclusion Pd-catalyzed cross-coupling reactions of

Synthesis of highly functionalized 2,2'-bipyridines by cyclocondensation of β-ketoenamides – scope and limitations

• Paul Hommes and
• Hans-Ulrich Reissig

Beilstein J. Org. Chem. 2016, 12, 1170–1177, doi:10.3762/bjoc.12.112

• couplings. Thus, a library of specifically substituted bipyridine derivatives was generated, showing the versatility of the simple 1,3-diketone-based approach to this important class of ligands. Keywords: 2,2-bipyridines; cross couplings; cyclocondensation; β-ketoenamides; nonaflates; Introduction In 2009

• using nonafluorobutanesulfonyl fluoride (NfF) as sulfonylating reagent. In subsequent publications we could demonstrate that this method can be used to synthesize a variety of functionalized pyridine derivatives, 2,2´-bipyridines or terpyridines [2][3][4]. An alternative entry to the crucial β

• this reaction sequence. For this purpose we prepared other β-ketoenamides, studied their cyclocondensation reactions and used the present functionalities for subsequent reactions, in particular palladium-catalyzed coupling reactions. 2,2´-Bipyridines are a very important class of ligands employed in

The simple production of nonsymmetric quaterpyridines through Kröhnke pyridine synthesis

• Isabelle Sasaki,
• Jean-Claude Daran and
• Gérard Commenges

Beilstein J. Org. Chem. 2015, 11, 1781–1785, doi:10.3762/bjoc.11.193

• asymmetrical analogues. Various coupling methodologies have also been developed: (i) the Ullmann reaction with copper powder at high temperature [9]; (ii) coupling of 6-halo-2,2’-bipyridines in the presence of nickel reagents [16][17], some of which are chiral [18][19]; and (iii) a Stille-based synthetic

Self-assembly of heteroleptic dinuclear metallosupramolecular kites from multivalent ligands via social self-sorting

• Christian Benkhäuser and
• Arne Lützen

Beilstein J. Org. Chem. 2015, 11, 693–700, doi:10.3762/bjoc.11.79

• cage-like homoleptic metal complexes is (almost) prevented when they are mixed with a suitable transition metal ion. As the metal ions we chose copper(I) ions which prefer a tetrahedral coordination sphere by two chelating ligands with N-donor centers such as 2,2'-bipyridines or 1,10-phenanthrolines

Towards allosteric receptors – synthesis of β-cyclodextrin-functionalised 2,2’-bipyridines and their metal complexes

• Christopher Kremer,
• Gregor Schnakenburg and
• Arne Lützen

Beilstein J. Org. Chem. 2014, 10, 814–824, doi:10.3762/bjoc.10.77

• Abstract Herein, we present three new 2,2’-bipyridines that carry two β-cyclodextrin moieties in different substitution patterns. When coordinated by zinc(II) or copper(I) ions (or their complexes), these compounds undergo conformational changes and switch between “open” and “closed” forms and thereby

• bringing together or separating the cyclodextrin moieties from each other. Keywords: allosteric receptors; 2,2’-bipyridines; β-cyclodextrin; supramolecular chemistry; metal complexes; Introduction In biological systems, recognition events play a major role to guarantee the selectivity of essential

• out of it [7][8][9][10][11][12][13][14]. 2,2’-Bipyridines have been demonstrated to be excellent artificial allosteric centres due to their well-known ability to switch between syn- and anti-conformations as an answer to an external stimulus [15]. This switching process can be controlled either by

True and masked three-coordinate T-shaped platinum(II) intermediates

• Manuel A. Ortuño,
• Salvador Conejero and
• Agustí Lledós

Beilstein J. Org. Chem. 2013, 9, 1352–1382, doi:10.3762/bjoc.9.153

• polymeric species (Scheme 19). Zucca and co-workers reported the synthesis of several cyclometalated compounds 44 by means of substitution and “rollover” processes (Scheme 20) [124]. Starting from derivative 41, DMSO displacement by 6-substituted 2,2’-bipyridines (NN ligands) yields the corresponding

A practical two-step procedure for the preparation of enantiopure pyridines: Multicomponent reactions of alkoxyallenes, nitriles and carboxylic acids followed by a cyclocondensation reaction

• Christian Eidamshaus,
• Roopender Kumar,
• Mrinal K. Bera and
• Hans-Ulrich Reissig

Beilstein J. Org. Chem. 2011, 7, 962–975, doi:10.3762/bjoc.7.108

• a chiral side chain as well as heteroaromatic units. 2,2’-Bipyridines with structures similar to 72 might show interesting properties when used as ligands in asymmetric transformations. The nonaflate moiety should allow electronic fine tuning of the ligand properties in palladium-catalyzed or

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

• soft materials with non-conventional structures. Platinum(II) and Zinc(II) For the less explored Pt(II) and Zn(II) metal centres versatile 2,2′-bipyridines have been selected since they are well-known building blocks for the formation of inorganic functional nanomaterials [51]. The complexation of non

• ] (Figure 4) to self-assemble into full disc shaped dimers as described by the complementary shape approach [52]. The appearance of mesomorphism is related to the length of the alkyl chains: indeed the complexes based on the 2,2′-bipyridines with short tails melted directly into an isotropic liquid, while

• time, order, mobility, and changes in molecular organization in response to external stimuli could be a good strategy for developing new soft materials for innovative applications. In this context the same 2,2′-bipyridines have been coordinated to Zn(II) ions where the tetrahedral geometry of the Zn(II