Platinum-catalyzed reaction of alkynes with ArI (Ar = aryl and thienyl) and Ar′SM (M = Na, K, and Sn(Bu-n)3): Three- vs two-component cross-coupling reaction

Article abstract of DOI:10.1021/om050340z

The Pt-catalyzed reactions of terminal alkynes HCCR (2) with ArI (6) (Ar = aryl and thienyl) and Ar′SM (M = Li, Na, K, and Sn(n-Bu₃)) (7) have been examined. Among them, the combined use of 2- and 3-iodothiophene with PhSK resulted in the formation of (Z)-Ar(H)C=C(SAr′)(R) (5) in moderate to good yields. When aryl iodide was employed as a coupling partner, thioether ArSAr′ (4), a direct cross-coupling product between 6 and 7, was competitively produced together with 5. The ratios of formation of 5/4 were significantly dependent on the substituent in Ar of 6 and Ar′ of 7 as well as species of 2. The mechanistic study indicated that 4 was produced by the alkyne-participated reaction of 6 with Pt(Ar)(SAr′)(PPh₃) ₂ (1).