1899-09-8Relevant academic research and scientific papers
Supramolecular hierarchy among halogen-bond donors
Aakeroey, Christer B.,Baldrighi, Michele,Desper, John,Metrangolo, Pierangelo,Resnati, Giuseppe
, p. 16240 - 16247 (2013/12/04)
Through a combination of structural chemistry, vibrational spectroscopy, and theory, we have systematically examined the relative structure-directing importance of a series of ditopic halogen-bond (XB) donors. The molecular electrostatic potential surfaces of six XB donors were evaluated, which allowed for a charge-based ranking. Each molecule was then co-crystallized with 21 XB acceptors and the results have made it possible to map out the supramolecular landscape describing the competition between I/Br-ethynyl donors, perfluorinated I/Br donors, and I/Br-phenyl based donors. The results offer practical guidelines for synthetic crystal engineering driven by robust and directional halogen bonds. Copyright
Highly diastereoselective C(sp3)i-C(sp) cross-coupling reactions between 1,3- and 1,4-substituted cyclohexylzinc reagents and bromoalkynes through remote stereocontrol
Thaler, Tobias,Guo, Li-Na,Mayer, Peter,Knochel, Paul
supporting information; experimental part, p. 2174 - 2177 (2011/04/25)
Under the influence: The use of the readily available and inexpensive orthophenantroline derivative neocuproine as a ligand in the generally applicable and highly stereoselective palladium-catalyzed title reaction results in diastereomeric ratios of up to 98:2. The method can be used for the synthesis of building blocks which may be relevant for the synthesis of liquid crystalline mesogens and their chiral dopants (see scheme, dba=trans,trans- dibenzylideneacetone).
Efficient synthesis of a complete donor/acceptor bis(aryl)diyne family
Holmes, Brian T.,Pennington, William T.,Hanks, Timothy W.
, p. 2447 - 2461 (2007/10/03)
A facile route to a family of bis(aryl)diynes containing both an electron donating pyridine ring and an electron accepting iodobenzene has been developed. The convergent synthesis involves the coupling of 2-, 3-, or 4-bromopyridine with TMS-acetylene, followed by deprotection to form the first half of the molecule. Similarly, 2-, 3-, or 4-iodoaniline was coupled to TMS-acetylene after protection of the amine group as a diethyltriazine. After conversion of the triazine to an iodine, deprotection of the acetylene and formation of the corresponding bromophenyl-acetylene, the two halves of the molecule were coupled under Cadiot-Chodkiewicz conditions. Nine new compounds were prepared, each of which was found to thermally polymerize from the melt. None of the compounds underwent photochemical polymerization in the solid-state.
