Synthesis 2018; 50(16): 3224-3230
DOI: 10.1055/s-0036-1591568
special topic
© Georg Thieme Verlag Stuttgart · New York

Iodine-Mediated Intramolecular C–H Amination of Benzimidazoles: A Metal-Free Route to Dihydroimidazobenzimidazoles

Pinaki Bhusan De
Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati 781039, India   Email: tpunni@iitg.ernet.in
,
Sourav Pradhan
Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati 781039, India   Email: tpunni@iitg.ernet.in
,
Tariq A. Shah
Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati 781039, India   Email: tpunni@iitg.ernet.in
,
Tharmalingam Punniyamurthy*
Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati 781039, India   Email: tpunni@iitg.ernet.in
› Author Affiliations
We thank Science and Engineering Research Board (EMR-2015-43) and Council of Scientific and Industrial Research [02(0255)-2016-EMR-II] for the financial support. T.A.S. thanks Science and Engineering Research Board (PDF/2017/002653) for financial support.
Further Information

Publication History

Received: 01 March 2018

Accepted after revision: 21 March 2018

Publication Date:
19 April 2018 (eFirst)

Published as part of the Special Topic Modern Coupling Approaches and their Strategic Applications in Synthesis

Abstract

Iodine-mediated cyclization of benzimidazolylethylamines in the presence of base to give dihydroimidazobenzimidazoles via a de­hydrogenative cross-coupling of C(sp2)–H and N–H bonds is reported. Metal-free conditions, preservation of the optical purity, and substrate scope are the important practical features.

Supporting Information

 
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