Synthesis of 2,2'-bipyridyl-type compounds via the Suzuki-Miyaura cross-coupling reaction
(Chemical Equation Presented) 2,2′-Bipyridyl-type compounds may be prepared by Suzuki-Miyaura coupling of a 2-pyridylboronic ester with 2-haloazines and -azoles. Ten examples are presented with yields of 47 to 84%. Both arylbromides and arylchlorides undergo the coupling, but the reaction is sensitive to ring substitution adjacent to the halogen.
Jones, Nicholas A.,Antoon, James W.,Bowie Jr., Alfred L.,Borak, J. Brian,Stevens, Erland P.
Adjacent-ring directed ortho metallation by the 2-pyridyl group in 2-pyridyldiazines
The first examples demonstrating the aptitude of 2-pyridyl group substituting diazines as Directing ortho-Metallation Group (DoMG) are described: three 2-pyridyldiazines were deuteriated via metallation with lithium-2,2,6,6-tetramethylpiperidide (LTMP) indicating promising ortho regioselectivities with respect to the Ar-Ar bond on the diazine ring.
Metallation of pyridin-2-yldiazines. Use of pyridine ring as ortho-directing group. Diazines. Part 45
Starting from commercial chlorodiazines, we report the synthesis of pyridin-2-yldiazines. The first lithiation and functionalization of these compounds are reported and the regioselectivity of the metallation is discussed. The functionalization via the metallation reaction, provides a new access to substituted pyridin-2-yldiazines, which could be used as building blocks in supramolecules.