Synthesis 2019; 51(13): 2678-2686
DOI: 10.1055/s-0037-1611534
special topic
© Georg Thieme Verlag Stuttgart · New York

Sterically Hindered Amination of Aryl Chlorides Catalyzed by a New Carbazolyl-Derived P,N-Ligand-Composed Palladium Complex

Wing In Lai
,
Man Pan Leung
,
Pui Ying Choy
,
Fuk Yee Kwong*
Department of Chemistry, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong   Email: fykwong@cuhk.edu.hk
› Author Affiliations
We thank the Research Grants Council of Hong Kong, General Research Fund (GRF 15303415/15P) and The Chinese University of Hong Kong (CUHK) Direct Grant (4442122) for financial support.
Further Information

Publication History

Received: 11 March 2019

Accepted after revision: 12 April 2019

Publication Date:
06 May 2019 (eFirst)

These authors contributed equally to this work.

Published as part of the Special Topic Amination Reactions in Organic Synthesis

Abstract

A family of 2-(9H-carbazol-9-yl)phenyl-based phosphine ligands were synthesized and their efficacy in promoting the steric hindered Buchwald–Hartwig amination was evaluated. In the presence of Pd(OAc)2 (0.03–1.0 mol%) associated with the newly developed a carbazolyl-derived phosphine ligand, the synthesis of tetra-ortho-substituted diarylamines proceeded smoothly with excellent product yields (up to 99%). A remarkable result was obtained even for the coupling of highly sterically congested 2,6-diisopropylaniline and hindered 2-chloro-1,3,5-triisopropylbenzene (96% isolated yield). A possible decomposition pathway for the anthracenyl C–N coupling product is also reported.

Supporting Information

 
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