Transition-metal-catalyzed regioselective aroyl-and trifluoro-acetylthiolation of alkynes using thioesters

Y Minami, H Kuniyasu, K Miyafuji…

Index: Minami, Yasunori; Kuniyasu, Hitoshi; Miyafuji, Kiyoshi; Kambe, Nobuaki Chemical Communications, 2009 , # 21 p. 3080 - 3082

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Citation Number: 15

Abstract

The attempted reaction of 1-octyne (1a; R = n-C 6 H 13 , 1.2 mmol) with Ar 1 C(O)SAr 2 (2a; Ar 1 = p-tolyl, Ar 2 = p-MeOC 6 H 4 , 1.0 mmol) in the presence of Pd(PPh 3 ) 4 (0.05 mmol) under toluene reflux gave an aroylthiolation product (Ar 1 C(O))(H)C C(n-C 6 H 13 )(SAr 2 ) (4a) in 10% yield (E/Z = 61/39) together with 50% of an Ar 1 SAr 2 (5a) 3 and 20% of a hydrothiolation product H 2 C C(n-C 6 H 13 )(SAr 2 ) (6a) 4 (entry 1, Table 1). The effects of various ...