Dissection of Alkylpyridinium Structures to Understand Deamination Reactions.
Dissection of Alkylpyridinium Structures to Understand Deamination Reactions.
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DOI：
10.1021/acscatal.1c01860
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发表时间：
2021-07-16
期刊：
影响因子：
12.9
通讯作者：
Kozlowski MC
中科院分区：
文献类型：
--
作者：
Tcyrulnikov S;Cai Q;Twitty JC;Xu J;Atifi A;Bercher OP;Yap GPA;Rosenthal J;Watson MP;Kozlowski MC
Via conversion to Katritzky pyridinium salts, alkyl amines can now be used as alkyl radical precursors for a range of deaminative functionalization reactions. The key step of all these methods is single electron reduction of the pyridinium ring, which triggers C–N bond cleavage. However, little has been done to understand how the precise nature of the pyridinium influences these events. Using a combination of synthesis, computation, and electrochemistry, this study delineates the steric and electronic effects that substituents have on the canonical steps and the overall process. Depending on the approach taken, consideration of both the reduction and the subsequent radical dissociation may be necessary. Whereas the electronic effects on these steps work in opposition to each other, the steric effects are synergistic, with larger substituents favoring both steps. This understanding provides a framework for future design of pyridinium salts to match the mode of catalysis or activation.
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DOI：
10.1055/s-0037-1610084
发表时间：
2018-08
期刊：
Synthesis
影响因子：
--
作者：
Guan W;Liao J;Watson MP
通讯作者：
Watson MP
影响因子：
21.8
作者：
Liu, Yongbing;Ge, Haibo
通讯作者：
Ge, Haibo
可见光驱动的四烷基铵盐的无外部还原剂交叉电偶合
影响因子：
15
作者：
Liao, Li-Li;Cao, Guang-Mei;Yu, Da-Gang
通讯作者：
Yu, Da-Gang
DOI：
10.1039/p19800001895
发表时间：
1980-01-01
期刊：
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
影响因子：
--
作者：
KATRITZKY, AR;THIND, SS
通讯作者：
THIND, SS
影响因子：
16.6
作者：
Li, Man-Bo;Wang, Yong;Tian, Shi-Kai
通讯作者：
Tian, Shi-Kai