Primary vs. secondary alkylpyridinium salts: a comparison under electrochemical and chemical reduction conditions
Literature Information
Publication Date
2023-07-21
DOI
10.1039/D3FD00120B
Impact Factor
4.008
Authors
Bria Garcia, Jessica Sampson, Mary P. Watson, Dipannita Kalyani
View Original
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.
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Source Journal
Faraday Discussions
CiteScore:
4.9
Self-citation Rate:
1.3%
Articles per Year:
166
Faraday Discussions covers a variety of topics in rapidly developing areas of the physical sciences, with a focus on physical chemistry and its interfaces with other scientific disciplines. The journal publishes the papers presented and a record of the questions, discussion and debate that took place at the corresponding Faraday Discussions meeting; and provides an important record of current international knowledge and opinions in the relevant field. Each Faraday Discussion covers a topic in a rapidly developing area of chemistry, and will be of interest to academic and industrial chemists across all areas of the chemical sciences.
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