Synthesis 2017; 49(07): 1623-1631
DOI: 10.1055/s-0036-1588921
paper
© Georg Thieme Verlag Stuttgart · New York

Regioselective Radical Arylation of Aromatic Diamines with Arylhydrazines

Toshihide Taniguchi*
a  Seika Corporation, 1-1-82 Kozaika, Wakayama 641-0007, Japan   Email: t-taniguchi@waseika.com
b  Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, 1-1 Gakuen-cho, Naka-ku, Sakai, Osaka 599-8531, Japan
,
Mitsutaka Imoto
a  Seika Corporation, 1-1-82 Kozaika, Wakayama 641-0007, Japan   Email: t-taniguchi@waseika.com
,
Motonori Takeda
a  Seika Corporation, 1-1-82 Kozaika, Wakayama 641-0007, Japan   Email: t-taniguchi@waseika.com
,
Takeo Nakai
c  Organic Materials Research Division, Osaka Municipal Technical Research Institute, 1-6-50 Morinomiya, Joto-ku, Osaka 536-8553, Japan   Email: tmizuno@omtri.or.jp
,
Masatoshi Mihara
c  Organic Materials Research Division, Osaka Municipal Technical Research Institute, 1-6-50 Morinomiya, Joto-ku, Osaka 536-8553, Japan   Email: tmizuno@omtri.or.jp
,
Takumi Mizuno*
c  Organic Materials Research Division, Osaka Municipal Technical Research Institute, 1-6-50 Morinomiya, Joto-ku, Osaka 536-8553, Japan   Email: tmizuno@omtri.or.jp
,
Akihiro Nomoto
b  Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, 1-1 Gakuen-cho, Naka-ku, Sakai, Osaka 599-8531, Japan
,
Akiya Ogawa
b  Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, 1-1 Gakuen-cho, Naka-ku, Sakai, Osaka 599-8531, Japan
› Author Affiliations
Further Information

Publication History

Received: 15 October 2016

Accepted after revision: 14 November 2016

Publication Date:
07 December 2016 (online)


Abstract

The arylation of aromatic diamines with arylhydrazine hydrochlorides was achieved in reasonable yields. This new and simple reaction occurred at room temperature in air using an inexpensive base. This transformation seems to proceed via a homolytic aromatic substitution (HAS) mechanism. The synthesized aromatic diamines are used as raw materials for polyimides, including important aerospace materials, for example, Kapton®.

Supporting Information

 
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