Tetrahedron

Highly regioselective hydroiodination of terminal alkynes and silylalkynes with iodine and phosphorus reagents leading to internal iodoalkenes

S Kawaguchi, H Masuno, M Sonoda, A Nomoto…

Index: Kawaguchi, Shin-Ichi; Masuno, Haruna; Sonoda, Motohiro; Nomoto, Akihiro; Ogawa, Akiya Tetrahedron, 2012 , vol. 68, # 47 p. 9818 - 9825

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Abstract

Markovnikov-type hydroiodination of terminal alkynes with iodine and Ph2P (O) H took place selectively to afford the corresponding internal iodoalkenes in good yields. Combination of (PhO) 2P (O) H and Ph2P (O) OH instead of Ph2P (O) H also provided internal iodoalkenes in excellent yields. This hydroiodination is advantageous in terms of mild conditions, convenient operation, and tolerance to various functional groups. In addition, direct ...