Synthesis 2020; 52(07): 1096-1102
DOI: 10.1055/s-0039-1690788
paper
© Georg Thieme Verlag Stuttgart · New York

Facile Synthesis of π-Conjugated Heteroaromatic Compounds via Weak-Base-Promoted Transition-Metal-Free C–N Coupling

Takahiro Senoo
,
Aiko Inoue
,
Keiji Mori
Department of Applied Chemistry, Graduate school of Engineering, Tokyo University of Agriculture and Technology, 2-24-16 Nakacho, Koganei, Tokyo 184-8588, Japan   Email: k_mori@cc.tuat.ac.jp
› Author Affiliations
This work was partially supported by a Grant-in-Aid for Scientific Research from the Japan Society for the Promotion of Science.
Further Information

Publication History

Received: 23 October 2019

Accepted after revision: 08 December 2019

Publication Date:
08 January 2020 (online)


Abstract

A K2CO3-promoted transition-metal-free C–N coupling reaction was developed. When a solution of 1-(2-aminophenyl)-8-iodo­naphthalenes in DMSO was treated with 2.5 equivalents of K2CO3 and 5.0 equivalents of MeI, intramolecular C–N coupling reaction proceeded smoothly even at low temperature (room temperature) to afford various heteroaromatic compounds in good chemical yields. Additional experiments suggested that this reaction might have proceeded through an unusual SNAr reaction between haloarenes and a bulky tertiary amine moiety.

Supporting Information