Synthesis

One-pot synthesis and functionalization of polyynes via alkylidene carbenoids

T Luu, Y Morisaki, RR Tykwinski

Index: Luu, Thanh; Morisaki, Yasuhiro; Tykwinski, Rik R. Synthesis, 2008 , # 7 p. 1158 - 1162

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Abstract

Abstract A one-pot, two-step method for the synthesis of diynes and triynes is reported. The reaction of a dibromoolefinic precursor with BuLi effects a Fritsch-Buttenberg-Wiechell rearrangement and generates a lithium acetylide intermediate, which is then trapped with a variety of electrophiles to produce substituted diynes and triynes. Alternatively, transmetalation from the lithium acetylide to give a zinc acetylide provides a nucleophilic ...