Qihao Jin, Yi-Jie Wang, Prof. Xinxin Wu, Prof. Jian-Ping Zou
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Phosphorylated Hydrazones and Diazophosphonate Synthesis Through Base-Promoted Radical Reactions
Herein, we report a regioselective phosphonylation of aldehyde-derived hydrazones via P-centered radical addition, expanding C─P bond formation to include dialkyl phosphites. Optimization studies established manganese acetate as an efficient oxidant and silver nitrate as the optimal catalyst, enabling mild and efficient radical phosphonylation. Notably, 4-methylbenzenesulfonylhydrazones underwent an unexpected transformation, affording diazo phosphonates instead of phosphonylated products. This study offers a practical and versatile method for C─P bond formation and provides new insights into radical-mediated hydrazone functionalization, with potential applications in pharmaceuticals and materials science.
期刊介绍:
Organic chemistry is the fundamental science that stands at the heart of chemistry, biology, and materials science. Research in these areas is vigorous and truly international, with three major regions making almost equal contributions: America, Europe and Asia. Asia now has its own top international organic chemistry journal—the Asian Journal of Organic Chemistry (AsianJOC)
The AsianJOC is designed to be a top-ranked international research journal and publishes primary research as well as critical secondary information from authors across the world. The journal covers organic chemistry in its entirety. Authors and readers come from academia, the chemical industry, and government laboratories.