214360-62-0Relevant academic research and scientific papers
Chemoselective Rhodium-Catalyzed Borylation of Bromoiodoarenes under Mild Conditions
Varni, Anthony J.,Bautista, Michael V.,Noonan, Kevin J.T.
, p. 6770 - 6777 (2020/07/21)
A chemoselective rhodium-catalyzed borylation has been developed for the preparation of aryl boronate esters. The reaction proceeds under mild conditions with excellent selectivity for C-I bonds in bromoiodoarenes and exhibits broad functional group tolerance. This procedure can act as a complementary approach toward bifunctional arenes along with other metal-catalyzed borylations. Additionally, the reaction's utility in the preparation of monomers for metal-catalyzed cross-coupling polymerization is demonstrated.
One-Pot Synthesis of a Linear [4]Catenate Using Orthogonal Metal Templation and Ring-Closing Metathesis
Amir, Faheem,Barnes, Jonathan C.,Chang, Christy,Colley, Nathan D.,Fisher, Jeremy M.,Greene, Angelique F.,Li, Lei,Li, Ruihan,Li, Xuesong,Nosiglia, Mark A.
supporting information, (2020/08/12)
The efficient synthesis of well-defined, linear oligocatenanes possessing multiple mechanical bonds remains a formidable challenge in the field of mechanically interlocked molecules. Here, a one-pot synthetic strategy is described to prepare a linear [4]catenate using orthogonal metal templation between a macrocycle precursor, composed of terpyridine and phenanthroline ligands spaced by flexible glycol linkers, and a closed phenanthroline-based molecular ring. Implementation of two simultaneous ring-closing metathesis reactions after metal complexation resulted in the formation of three mechanical bonds. The linear [4]catenate product was isolated in 55% yield as a mixture of topological diastereomers. The intermediate metal complexes and corresponding interlocked products (with and without metals) were characterized by nuclear magnetic resonance, mass spectrometry, gel permeation chromatography, and UV-vis absorption spectroscopy. We envision that this general synthetic strategy may pave the way for the synthesis of higher order linear oligocatenates/catenanes with precise molecular weights and four or more interlocking molecular rings.
Linear bilateral extended 2,2′:6′,2′′-terpyridine ligands, their coordination complexes and heterometallic supramolecular networks
Veliks, Janis,Tseng, Jui-Chang,Arias, Karla I.,Weisshar, Florian,Linden, Anthony,Siegel, Jay S.
, p. 4317 - 4327 (2015/01/08)
Octahedral metal complexes of tridentate 2,2′:6′,2′′-terpyridine (terpy) fused with five-membered furan rings mimic the topology of tetrahedral metal complexes of bidentate 5,5′-functionalized 2,2′-bipyridine (bipy). Herein, we report the robust synthesis of 2,6-bis(2-substituted-furo[2,3-c]pyridine-5-yl)pyridine based ligands to access a series of linear bilateral extended terpy derivatives. This molecular design of alternating five- and six-membered rings has been applied to extend the applicability of terpy as a building block in supramolecular chemistry. The complexation of 2,6-bis(2-substituted-furo[2,3-c]pyridine-5-yl)pyridine derivatives with metal ions preferring octahedral geometry (Fe2+, Ru2+, and Zn2+) gives molecular "crossings" and "corners". Such design elements, functionalized with 4-pyridyl groups, allowed the construction of 3D and 2D heterometallic supramolecular networks containing Fe2+, Ag+or Fe2+, Cu+metal centers.
Asymmetric synthesis of 1-heteroaryl-1-arylalkyl tertiary alcohols and 1-pyridyl-1-arylethanes by lithiation-borylation methodology
Watson, Charlotte G.,Aggarwal, Varinder K.
supporting information, p. 1346 - 1349 (2013/05/09)
The synthesis of highly enantioenriched α-heterocyclic tertiary alcohols has been achieved via lithiation-borylation of a configurationally stable lithiated carbamate and heterocyclic pinacol boronic esters followed by oxidation. Protodeboronation of the α-heterocyclic tertiary boronic esters using TBAF·3H2O or CsF gave highly enantioenriched 1-pyridyl-1-arylethanes in high er.
Synthesis of novel halopyridinylboronic acids and esters. Part 1: 6-Halopyridin-3-yl-boronic acids and esters
Bouillon, Alexandre,Lancelot, Jean-Charles,Collot, Valérie,Bovy, Philippe R,Rault, Sylvain
, p. 2885 - 2890 (2007/10/03)
This paper describes a general method for the synthesis and isolation of novel 6-halo-pyridin-3-yl-boronic acids and esters 2-5. These compounds are prepared taking in account a regioselective halogen-metal exchange with a trialkylborate starting from 2,5-dihalopyridines. All substrates studied to date provided a single regioisomeric boronic acid or ester product. Additionally, these compounds have been found to undergo Pd-catalysed coupling with a range of arylhalides and authorise a strategy to produce new pyridines libraries.
