Wolff Rearrangement of α-Diazoketones Using in Situ Generated Silver Nanoclusters as Electron Mediators

Wolff Rearrangement of α-Diazoketones Using in Situ Generated Silver Nanoclusters as Electron Mediators

We report Wolff rearrangement of α-diazoketones by in situ generated silver nanoclusters (Ag n , 2−4 nm) from silver(I) oxide (Ag2O) involving a nonclassical electron-transfer process. Our results show that Ag n +/Ag n 0 redox couple allows the initial removal of an electron from α-diazoketone and i...

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Veröffentlicht in:Organic letters 2006-03, Vol.8 (6), p.1089-1092
Hauptverfasser: Sudrik, Surendra G, Sharma, Jadab, Chavan, Vilas B, Chaki, Nirmalya K, Sonawane, Harikisan R, Vijayamohanan, Kunjukrishna P
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container_end_page 1092
container_issue 6
container_start_page 1089
container_title Organic letters
container_volume 8
creator Sudrik, Surendra G
Sharma, Jadab
Chavan, Vilas B
Chaki, Nirmalya K
Sonawane, Harikisan R
Vijayamohanan, Kunjukrishna P
description We report Wolff rearrangement of α-diazoketones by in situ generated silver nanoclusters (Ag n , 2−4 nm) from silver(I) oxide (Ag2O) involving a nonclassical electron-transfer process. Our results show that Ag n +/Ag n 0 redox couple allows the initial removal of an electron from α-diazoketone and its back-donation after chemical reaction(s). Controlled potential coulometry (CPC) of various α-diazoketones results in the realization of Wolff-rearranged carboxylic acids in excellent yields.
doi_str_mv 10.1021/ol052981w
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title Wolff Rearrangement of α-Diazoketones Using in Situ Generated Silver Nanoclusters as Electron Mediators
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