Synthesis of allenes via CuBr-catalyzed homologation of alk-1-ynes accelerated by microwave

H Nakamura, T Sugiishi, Y Tanaka

Index: Nakamura, Hiroyuki; Sugiishi, Tsuyuka; Tanaka, Yuko Tetrahedron Letters, 2008 , vol. 49, # 50 p. 7230 - 7233

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Citation Number: 26

Abstract

CuBr-catalyzed homologation of alk-1-ynes 1 with paraformaldehyde and N, N- diisopropylamine (or N, N-dicyclohexylamine) was accelerated by microwave irradiation at 150° C to afford the corresponding allenes 2 in good to high yields in 1–10min. Bisalkynes 5 and 7 were also converted to the corresponding bisallenes 6 and 8 in 63% and 61% yields, respectively, under the current condition.