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Ni-Catalyzed Deamination Cross-Electrophile Coupling of Katritzky Salts with Halides via C–N Bond Activation

preprint
submitted on 28.01.2019, 17:59 and posted on 28.01.2019, 19:29 by Shengyang Ni, Chunxiao Li, Jianlin Han, Yu Mao, Yi Pan
This work describes the first Ni-catalyzed cross-electrophile coupling of alkylpyridinium salts, derived from the corresponding amines, with aryl iodide, bromoalkyne or bromoalkyl coupling partners. C(sp)-C(sp3), C(sp2)-C(sp3) and C(sp3)-C(sp3) bond formation was achieved to afford a variety of synthetically useful arenes, alkynes and alkanes in good yields from2-33. The advantages of the methodology are showcased in the two-step synthesis of the key lactonic moiety of (+)-Compactin and (+)-Mevinolin from commercially available starting materials. A one-pot procedure without isolation of alkylpyridinium tetrafluoroborate salt was also demonstrated to be successful. This work represents a new strategy for the cross-coupling reaction of two electrophiles, and also provides a complementary and highly valuable vista for the current methodologies of alkyl arene/alkyne/alkane synthesis.

Funding

National Natural Science Foundation of China (No 21761132021)

History

Email Address of Submitting Author

hanjl@njfu.edu.cn

Institution

Nanjing University

Country

China

ORCID For Submitting Author

0000-0002-3817-0764

Declaration of Conflict of Interest

no conflict of interest

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