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.
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).
Hazard Statements: H315-H319-H335
Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P260-P201-P280g-P304+P340-P405-P501a
Do not breathe dust/fume/gas/mist/vapours/spray. Obtain special instructions before use. Wear protective gloves. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.