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. 2020 Jun 23;5(26):15936-15941.
doi: 10.1021/acsomega.0c01124. eCollection 2020 Jul 7.

Enantioselective C,P-Palladacycle-Catalyzed Arylation of Imines

Yinhua Huang  1 , Lijun Wang  1 , Junbao Li  1 , Huayu Qiu  1 , Pak-Hing Leung  2
Affiliations

Enantioselective C,P-Palladacycle-Catalyzed Arylation of Imines

Yinhua Huang et al. ACS Omega. .

Abstract

Chiral diarylmethylamines are of great interest because of their prevalence in biological and pharmaceutical sciences. Herein, we report a C,P-palladacycle-catalyzed enantioselective synthesis of chiral diarylmethylamines via asymmetric arylation of N-protected imines with arylboronic acids. The C,P-palladacycle showed high reactivity (up to 99% yield) and enantioselectivity (up to 99% ee) toward this arylation, enabling the tolerance of a wide range of functionalities, providing a convenient and efficient access to enantiomerically enriched diarylmethylamines. The absolute configuration of the product was well rationalized by the proposed stereochemical pathway and the catalytical cycle.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Figure 1
Figure 1
Selective examples of commercial drugs and bioactive molecules containing diarylmethylamine motifs.
Scheme 1
Scheme 1. Arylation of Imines Catalyzed by a C,P-Palladacycle
Scheme 2
Scheme 2. Proposed Catalytic Cycle for the Arylation of 1a with PhB(OH)2 Catalyzed by (S)-L2-Pd
Figure 2
Figure 2
Proposed stereochemical pathway for the arylation of 1a with PhB(OH)2 catalyzed by (S)-L2-Pd.
Scheme 3
Scheme 3. Competition Experiments
See this image and copyright information in PMC

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