Tetrahedron letters

Palladium catalyzed reaction of 2-alkynylanilines with allyl chlorides. Formation of 3-allylindoles

K Iritani, S Matsubara, K Utimoto

Index: Iritani, Koji; Matsubara, Seijiro; Utimoto, Kiitiro Tetrahedron Letters, 1988 , vol. 29, # 15 p. 1799 - 1802

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Citation Number: 190

Abstract

Abstract Pd (II) catalyzed reaction of N-carbomethoxy-2-alkynylanilines with allyl chlorides produces 2-alkyl-3-allyl-N-carbomethoxyindoles in the presence of oxirances; Aminopalladation of a N-carbomethoxy-2-alkynylaniline gives 3-(N-carbomethoxyindolyl) palladium intermediate, which regioselectively attacks on the γ position of chlorides to give 3- allyl-2-alkylindoles with concurrent regeneration of Pd (II) catalyst.

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