Volume 247, 2023

Primary vs. secondary alkylpyridinium salts: a comparison under electrochemical and chemical reduction conditions

Abstract

This report details a systematic comparison of the scope of aryl bromides in nickel-catalyzed, reductive cross-electrophile couplings of primary vs. secondary alkylpyridinium salts using both electrochemical and chemical reductants. Facilitated by the use of high-throughput experimentation (HTE) techniques, 37 aryl bromides, including 13 complex, drug-like examples, were investigated. By using primary and secondary substrates differing only by one methylene, we observed that the trends in ArBr scope are similar between the primary and secondary alkylpyridinium salts, although distinctions were observed in isolated cases. In addition, the electrochemical conditions compared favorably to those using chemical reductants, especially among the more complex, drug-like aryl halides.

Graphical abstract: Primary vs. secondary alkylpyridinium salts: a comparison under electrochemical and chemical reduction conditions

Associated articles

Supplementary files

Article information

Article type
Paper
Submitted
13 6 2023
Accepted
06 7 2023
First published
21 7 2023

Faraday Discuss., 2023,247, 324-332

Author version available

Primary vs. secondary alkylpyridinium salts: a comparison under electrochemical and chemical reduction conditions

B. Garcia, J. Sampson, M. P. Watson and D. Kalyani, Faraday Discuss., 2023, 247, 324 DOI: 10.1039/D3FD00120B

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