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Short Paper | Special issue | Vol 97, No. 2, 2018, pp.1175-1190
Published online, 3rd April, 2018
DOI: 10.3987/COM-18-S(T)62
Intramolecular Heck Insertion of a Diene-Allylic Amination Cascade to Synthesize a 2-Alkenyl-3,4-fused Indole Structure

Takahito Kuribara, Jun Ueda, Yuito Tanaka, Masaya Nakajima, Shingo Harada, and Tetsuhiro Nemoto*

*Pharmaceutical Chemistry, Graduate School of Pharmaceutical Sciences, Chiba University, 1-8-1 Inohana, Chuo, Chiba, Japan

Abstract

Iodoanilines bearing a diene side-chain at the 3-position were converted to tricyclic fused indole derivatives under palladium catalysis. This cascade reaction proceeds through an intramolecular Heck insertion of the diene, followed by an allylic amination reaction sequence. Experimental and computational studies indicated that 3--allyl palladium complex-mediated substitution was operative for the latter cyclization.