Studies on pyrimidine derivatives. VII. Nickel-phosphine complex-catalyzed Grignard coupling of chloropyrimidines.

Grignard Reactions Involving Halogenated Pyrimidines

“…The cross‐coupling of 4‐chloro‐2,6‐dimethylpyrimidine 31 with both alkyl and aryl Grignard reagents under similar conditions has also been reported to give products 32 , 33 , 34 (Scheme ).…”

“…The cross-coupling of 4-chloro-2,6-dimethylpyrimidine 31 with both alkyl and aryl Grignard reagents under similar conditions has also been reported to give products 32-34 [13] (Scheme 8). One example that is not a classical Grignard reagent involves the use of lithium tri(quinolinyl)magnesate 35, prepared by treatment of 3-bromoquinoline with lithiumtributylmagnesate.…”

“…Other examples of 2‐chloropyrimidines have been explored. Thus, 2‐chloro‐4,6‐dimethylpyrimidine 20 , treated with alkyl or aryl magnesium halides in the presence of Ni(dppe)Cl 2 or Ni(dppp)Cl 2 , affords moderate yields of cross‐coupled products 21 , 22 , 23 , 24 , 25 , 26 (Scheme ).…”

Ferrocenyl phosphane nickel carbonyls: Synthesis, solid state structure, and their use as catalysts in the oligomerization of ethylene

“…Nickel phosphanes have attracted considerable interest in recent years because they can be applied successfully in homogeneous catalysis including the polymerization of formaldehyde [1,2], dimerization of propene [3][4][5][6][7][8][9][10][11], synthesis of a-olefines [12][13][14][15][16][17][18][19], asymmetric hydrocyanation of styrene [20,21], hydrogenolysis of biphenylene [22,23], and the coupling of Grignard reagents with chloropyrimidines [24,25] and aryl chlorides [26,27]. Due to their diverse applications in the field of material sciences, e.g.…”

Nickel Catalyzed Coupling of Organic Halides and Related Reactions

“…'124 ' 158 ' 205 quinoline,163 pyrimidine,146 ' 158 benzothiazole,158 thiophene155 and furan158 (equations 88-92). One The reaction is not confined to organic halides and examples have been reported involving allyl alcohols, 130 " 132 ' 147 ethers, 120 ' 144 ' 155 sulphides 142 ' 143 ' 145 ' 158 and selenides 156 (equations 94-98).…”