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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 and posted on 28.01.2019 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

Exports