Pd-Catalyzed sulfinylzincation of activated alkynes with 1-alkynyl sulfoxides as a sulfinyl source

N Maezaki, S Yagi, R Yoshigami, J Maeda…

Index: Maezaki, Naoyoshi; Yagi, Suguru; Yoshigami, Ryoko; Maeda, Jun; Suzuki, Tomoko; Ohsawa, Shizuka; Tsukamoto, Kouji; Tanaka, Tetsuaki Journal of Organic Chemistry, 2003 , vol. 68, # 14 p. 5550 - 5558

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Citation Number: 27

Abstract

Unprecedented Pd-catalyzed sulfinylzincation with 1-alkynyl sulfoxide as a sulfinyl source was developed. Bis-sulfinyl alkenes were formed in good yields on treatment of 1-alkynyl sulfoxides with Et2Zn in the presence of a Pd-catalyst, wherein zinc sulfenate (or sulfinylzinc) species would be generated in situ to undergo highly syn-selective conjugate addition to the 1-alkynyl sulfoxides. By using 3, 3-dimethyl-1-butynyl sulfoxides, formation ...