Synthesis of Differently Disubstituted 2,2′‐Bipyridines by a Modified Negishi Cross‐Coupling Reaction

Abstract

A general practical approach to a number of differently disubstituted 2,2′‐bipyridines from substituted 2‐bromo‐ and 2‐chloropyridines by application of modified Negishi cross‐coupling conditions has been developed. These 2,2′‐bipyridines carry versatile functional groups that can be elaborated further, as demonstrated for some examples. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

Synthesis of 9,9′‐Spirobifluorenes and 4,5‐Diaza‐9,9′‐spirobifluorenes and Their Application as Affinity Materials for Quartz Crystal Microbalances

“…Therefore, we first followed aprotocol of Murakami et al to prepare 2-bromo-5-hydroxypyridine (11)a nd 2-bromo-5-methoxypyridine (12). [22] Finally,c ompound 13 was converted into the desired iodinated bipyridine 10 through ipso substitution. [22] Finally,c ompound 13 was converted into the desired iodinated bipyridine 10 through ipso substitution.…”

Synthesis and Photophysical Properties of Substituted 2,2′:6′,2′′‐Terpyridine Derivatives and Analogous Compounds with a Central Thiophene Ring

“…[10] Intermediate 5 could not be isolated, but its formation was clearly indicated by highresolution mass spectrometry.L ützen and co-workers similarly reported difficulties in isolating astructurally related 2,2'-bipyridylboronate. [11] Intermediate 5 was directly combined with pentafluorophenylh alides and the appropriate catalyst and typical additives for Suzuki-Miyaura couplings. With pentafluorophenyl bromide, only am ixture of terpyridine derivatives was obtained,w hich were not sufficiently stable to be purified and characterized, whereas the use of pentafluorophenyl iodide led to completed ecomposition of the precursor compounds.…”

Recent Advance in Heterocyclic Organozinc and Organomanganese Compounds; Direct Synthetic Routes and Application in Organic Synthesis

“…Most of the 2-pyridyl derivatives have been prepared using the Suzuki [ 11 , 12 , 13 , 14 ], Stille [ 15 , 16 , 17 ], Grignard [ 18 , 19 , 20 ], and Negishi [ 21 , 22 , 23 , 24 ] coupling reactions in the presence of a transition metal catalyst. Among these, the Suzuki coupling reaction is the most intensively studied and a very extensive body of work has been developed in this area [ 25 ].…”