2-[N,N-Bis(trifluoromethylsulfonyl)amino]-5-chloropyridine provides good yields of vinyl triflates from the corresponding ketone enolates or dienolates. It is used in the total synthesis of (-)-porantheridine and the trans decahydroquinoline alkaloid (+)-219A. It is also used as a reactant for Suzuki-Miyaura cross coupling, synthesis of nicotinic acetylcholine receptor-selective ligands, enantioselective desymmetrizing palladium catalyzed carbonylation reactions, synthesis of high affinity niacin receptor GPR109A agonists and in preparation of heteroaromatics.
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
Applications
2-[N,N-Bis(trifluoromethylsulfonyl)amino]-5-chloropyridine provides good yields of vinyl triflates from the corresponding ketone enolates or dienolates. It is used in the total synthesis of (-)-porantheridine and the trans decahydroquinoline alkaloid (+)-219A. It is also used as a reactant for Suzuki-Miyaura cross coupling, synthesis of nicotinic acetylcholine receptor-selective ligands, enantioselective desymmetrizing palladium catalyzed carbonylation reactions, synthesis of high affinity niacin receptor GPR109A agonists and in preparation of heteroaromatics.
Solubility
Reacts with water.
Notes
Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Store under dry inert gas. It is sensitive to moisture.
RUO – Research Use Only
Haruhiko Fuwa Dr.; Shinya Naito.; Tomomi Goto.; Makoto Sasaki Prof. Dr. Total Synthesis of (+)-Neopeltolide. Angewandte Chemie International Edition. 2008, 47 (25), 4737-4739.
Samantha J. Bamford.; Tim Luker.; W. Nico Speckamp.; Henk Hiemstra. Enantioselective Formal Total Synthesis of Roseophilin. Org. Lett. 2000, 2 (8), 1157-1160.
Highly reactive triflating agent which converts lithium enolates of ketones to vinyl triflates rapidly at low temperatures: Tetrahedron Lett., 33, 6299 (1992). Used in the total synthesis of (-)-porantheridine: J. Am. Chem. Soc. 115, 8851 (1993), and the trans decahydroquinoline alkaloid (+)-219A: J. Org. Chem., 60, 794 (1995).