Palladium-Catalyzed Hiyama-Type Coupling of Thianthrenium and Phenoxathiinium Salts
Zhi-Wei Cao1, Ji-Xuan Zhang1, Jin-Tao Wang1
1College of Chemistry and Molecular Sciences, Henan University, Kaifeng 475004, P. R. China.
Abstract:
Here, we demonstrate palladium-catalyzed Hiyama-type cross-coupling reactions of aryl thianthrenium or phenoxathiinium salts. By employing stable and inexpensive organosilanes, the arylation, alkenylation, and alkynylation were realized in high efficiency using commercially available Pd(Bu3P)2 as the catalyst, thus providing a reliable method for preparation of biaryls, styrenes, and aryl acetylenes with a broad functional group tolerance under mild conditions. Given the accessibility of aryl thianthrenium or phenoxathiinium salts from simple arenes in a remarkable regioselective fashion, this protocol also provides an attractive approach for the late-stage modification of complex bioactive scaffolds.
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