Selective stille coupling reactions of 3-chloro-5-halo(pseudohalo)-4 H -1,2,6-thiadiazin-4-ones
Date
2011ISSN
1523-7060Source
Organic lettersVolume
13Issue
21Pages
5886-5889Google Scholar check
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A series of 3-chloro-5-halo(pseudohalo)-4H-1,2,6-thiadiazin-4-ones (halo/pseudohalo = Br, I, OTf) are prepared from 3,5-dichloro-4H-1,2,6- thiadiazin-4-one (3) in good yields. Of these the triflate reacts with tributyltin arenes (Stille couplings) chemoselectively to give only the 5-aryl-3-chloro-4H-1,2,6-thiadiazin-4-ones in high yields. This allowed the preparation of a series of unsymmetrical biaryl thiadiazines and ultimately a series of oligomers. Furthermore, treatment of 3-chloro-5-iodo-4H-1,2,6- thiadiazin-4-one (10) with Bu3SnH and Pd(OAc)2 gave the bithiadiazinone which can also be further arylated via the Stille reaction to give bisthien-2-yl and bis(N-methylpyrrol-2-yl) analogs. © 2011 American Chemical Society.