Catalytic amination of 2-substituted pyridines with hydrazine derivatives.
[reaction in text] Protected pyridylhydrazine derivatives were prepared in a one-step palladium-catalyzed amination reaction using chelating phosphine ligands. 2-Pyridyl chlorides, bromides, and triflates were effective electrophiles in these reactions. Di-tert-butyl hydrazodiformate was an excellent hydrazine substrate, and the resulting products were deprotected under mild conditions. Catalytic amination provides a direct route to protected bifunctional hydrazinopyridine linkers that are suitable for metal-bioconjugate syntheses.
Arterburn
J B
JB
Department of Chemistry and Biochemistry, MSC 3C, New Mexico State University, P.O. Box 30001, Las Cruces, New Mexico 88003, USA. jarterbu@nmsu.edu
Rao
K V
KV
Ramdas
R
R
Dible
B R
BR
D000586:Amination; D002384:Catalysis; D002614:Chelating Agents / Q000737:chemistry; D006834:Hydrazines / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry; D010165:Palladium / Q000737:chemistry; D011725:Pyridines / Q000138:chemical synthesis / Q000737:chemistry*; D013329:Structure-Activity Relationship
D002614:Chelating Agents; D006834:Hydrazines; D009942:Organometallic Compounds; D011725:Pyridines; D010165:Palladium