Pd(II)-Catalyzed Directing-Group-Aided C–H Arylation and Alkylation of Pyrene Core: Synthesis of C1,C2- and C1,C10-Disubstituted Pyrene Motifs

Arup Dalal; Srinivasarao Arulananda Babu

doi:10.1055/a-1472-0881

Synthesis, Table of Contents

Synthesis 2021; 53(18): 3307-3324
DOI: 10.1055/a-1472-0881

special topic

Bond Activation – in Honor of Prof. Shinji Murai

Pd(II)-Catalyzed Directing-Group-Aided C–H Arylation and Alkylation of Pyrene Core: Synthesis of C1,C2- and C1,C10-Disubstituted Pyrene Motifs

Authors

Arup Dalal
Srinivasarao Arulananda Babu ∗

Abstract

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Abstract

We report the application of the Pd(II)-catalyzed, directing-group-aided C–H arylation/alkylation tactics to functionalize the pyrene core, especially, the relatively inaccessible C2 and K-region C10 positions of the pyrene core and augmentation of the library of pyrene derivatives with C1,C2- and C1,C10-disubstituted pyrene motifs. The Pd(II)-catalyzed β-C–H arylation/alkylation of the C2-position of pyrene-1-carboxamide possessing an 8-aminoquinoline directing group yielded various C1,C2-disubstituted pyrenes. Similarly, the Pd(II)-catalyzed selective γ-C–H arylation/alkylation of the C10-position of N-(pyren-1-yl)picolinamide, possessing a picolinamide directing group, yielded various C1,C10-disubstituted pyrenes. Examples of C(9)–H arylation of pyrene-1-carboxamide and the removal of the directing group after the C–H arylation/alkylation reactions were also shown. The structures of representative pyrene derivatives were confirmed by the X-ray structure analysis. Given the importance of the pyrene derivatives in various fields of chemical sciences, this report is a contribution towards augmentation of the library of pyrene derivatives with C1,C2- and C1,C10-disubstituted pyrene amide motifs.

Key words

C–H activation - C–H arylation/alkylation - C–H functionalization - bidentate directing group - carboxamides - palladium - pyrene

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References

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20 CCDC 2068244 (4a), 2068245 (4e), 2068246 (5n), and 2068247 (12c) contain the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures.

Supplementary Material

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