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Systematic Evaluation of 2-Arylazocarboxylates and 2-Arylazocarboxamides as Mitsunobu Reagents

Daisuke Hirose, Martin Gazvoda, Janez Košmrlj* and Tsuyoshi Taniguchi*

*University of Ljubljana, Večna pot 113, SI-1000 Ljubljana, Slovenia; Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan, Email: janez.kosmrljfkkt.uni-lj.si, tsuyoship.kanazawa-u.ac.jp

D. Hirose, M. Gazvoda, J. Košmrlj, T. Taniguchi, J. Org. Chem., 2018, 83, 4714-4729.

DOI: 10.1021/acs.joc.8b00486 (free Supporting Information)


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Abstract

2-Arylazocarboxylate and 2-arylazocarboxamide derivatives, which offer high thermal stability, have an excellent ability as Mitsunobu reagents. These reagents show similar or superior reactivity as compared to the known azo reagents in the conversion of a broad range of substrates. A one-pot iron-catalyzed aerobic oxidation enable a convenient recovery of these azo reagents.

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Key Words

Mitsunobu Reaction


ID: J42-Y2018